# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rm2128c_a
_database_code_depnum_ccdc_archive 'CCDC 2125083'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_C__Users_yarav_ONEDRI~1_CRYSTA~1_21DATA~1_RM2128 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: This was a small, weakly diffracting crystal. Despite using long
exposure times, high angle data exhibited I/s < 3. These data were largely
omitted in the latter stages of refinement, while maintaining sufficient
data to provide a data:parameter ratio of ca 10:1.

;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   26.505(6)
_cell_length_b                   5.5966(7)
_cell_length_c                   9.4104(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.519(15)
_cell_angle_gamma                90
_cell_volume                     1380.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1297
_cell_measurement_theta_min      3.8850
_cell_measurement_theta_max      20.1380

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7061
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.723
_diffrn_reflns_theta_max         22.496
_diffrn_reflns_theta_full        22.496
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1786
_reflns_number_gt                1056
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    mercury
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+1.1777P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1786
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2072
_refine_ls_wR_factor_gt          0.1669
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21828(14) 0.8787(6) 0.1394(3) 0.0677(11) Uani 1 1 d . . . . .
O3 O 0.44783(17) 0.4693(7) 0.0910(4) 0.0842(13) Uani 1 1 d . . . . .
N2 N 0.26208(18) 0.5925(7) 0.2812(4) 0.0579(12) Uani 1 1 d . . . . .
N1 N 0.19236(19) 0.7779(8) 0.3519(4) 0.0683(14) Uani 1 1 d D . . . .
H1 H 0.201(2) 0.699(8) 0.431(3) 0.082 Uiso 1 1 d D U . . .
C21 C 0.3081(2) 0.5913(8) 0.2220(5) 0.0543(14) Uani 1 1 d . . . . .
C26 C 0.3349(2) 0.3832(8) 0.2736(5) 0.0587(15) Uani 1 1 d . . . . .
C17 C 0.2229(2) 0.7595(10) 0.2502(5) 0.0604(14) Uani 1 1 d . . . . .
C22 C 0.3284(2) 0.7502(8) 0.1331(5) 0.0583(14) Uani 1 1 d . . . . .
H22 H 0.310737 0.887700 0.100240 0.070 Uiso 1 1 calc R U . . .
C11 C 0.1447(2) 0.8982(10) 0.3380(5) 0.0623(15) Uani 1 1 d . . . . .
C24 C 0.4018(2) 0.4958(9) 0.1415(6) 0.0643(15) Uani 1 1 d . . . . .
C27 C 0.3045(2) 0.2569(9) 0.3630(5) 0.0660(16) Uani 1 1 d . . . . .
H27 H 0.312829 0.112830 0.409961 0.079 Uiso 1 1 calc R U . . .
C28 C 0.2617(2) 0.3852(9) 0.3666(5) 0.0657(16) Uani 1 1 d . . . . .
H28 H 0.235657 0.343329 0.417953 0.079 Uiso 1 1 calc R U . . .
C23 C 0.3749(2) 0.7007(9) 0.0949(5) 0.0644(15) Uani 1 1 d . . . . .
H23 H 0.388988 0.807348 0.035900 0.077 Uiso 1 1 calc R U . . .
C25 C 0.3825(2) 0.3366(9) 0.2323(5) 0.0660(16) Uani 1 1 d . . . . .
H25 H 0.400901 0.200994 0.265361 0.079 Uiso 1 1 calc R U . . .
C12 C 0.1335(3) 1.0985(10) 0.2549(5) 0.0735(17) Uani 1 1 d . . . . .
H12 H 0.157389 1.161843 0.202353 0.088 Uiso 1 1 calc R U . . .
C16 C 0.1086(3) 0.8100(11) 0.4177(6) 0.0792(18) Uani 1 1 d . . . . .
H16 H 0.116560 0.677073 0.476016 0.095 Uiso 1 1 calc R U . . .
C13 C 0.0860(3) 1.2053(12) 0.2505(7) 0.096(2) Uani 1 1 d . . . . .
H13 H 0.078319 1.341018 0.194394 0.115 Uiso 1 1 calc R U . . .
C15 C 0.0615(3) 0.9148(14) 0.4121(7) 0.097(2) Uani 1 1 d . . . . .
H15 H 0.037727 0.851431 0.465105 0.116 Uiso 1 1 calc R U . . .
C29 C 0.4769(3) 0.2599(10) 0.1319(8) 0.102(2) Uani 1 1 d . . . . .
H29A H 0.485263 0.254406 0.234664 0.154 Uiso 1 1 calc R U . . .
H29B H 0.507774 0.263172 0.089807 0.154 Uiso 1 1 calc R U . . .
H29C H 0.457371 0.121107 0.098805 0.154 Uiso 1 1 calc R U . . .
C14 C 0.0496(3) 1.1139(15) 0.3278(7) 0.104(2) Uani 1 1 d . . . . .
H14 H 0.017756 1.185819 0.322738 0.125 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.228(6) . ?
O3 C24 1.380(7) . ?
O3 C29 1.424(6) . ?
N2 C17 1.396(7) . ?
N2 C28 1.412(6) . ?
N2 C21 1.415(7) . ?
N1 C17 1.346(7) . ?
N1 C11 1.420(7) . ?
C21 C22 1.383(7) . ?
C21 C26 1.412(7) . ?
C26 C25 1.399(7) . ?
C26 C27 1.434(7) . ?
C22 C23 1.362(7) . ?
C11 C12 1.374(7) . ?
C11 C16 1.390(8) . ?
C24 C25 1.384(7) . ?
C24 C23 1.387(7) . ?
C27 C28 1.347(7) . ?
C12 C13 1.389(8) . ?
C16 C15 1.374(8) . ?
C13 C14 1.388(9) . ?
C15 C14 1.377(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O3 C29 117.8(5) . . ?
C17 N2 C28 127.0(5) . . ?
C17 N2 C21 125.4(4) . . ?
C28 N2 C21 107.4(4) . . ?
C17 N1 C11 126.2(4) . . ?
C22 C21 C26 121.2(5) . . ?
C22 C21 N2 132.1(5) . . ?
C26 C21 N2 106.7(4) . . ?
C25 C26 C21 119.1(5) . . ?
C25 C26 C27 132.8(5) . . ?
C21 C26 C27 108.1(5) . . ?
O1 C17 N1 124.6(5) . . ?
O1 C17 N2 121.2(5) . . ?
N1 C17 N2 114.2(5) . . ?
C23 C22 C21 118.5(5) . . ?
C12 C11 C16 119.2(6) . . ?
C12 C11 N1 123.6(6) . . ?
C16 C11 N1 117.1(5) . . ?
O3 C24 C25 124.7(5) . . ?
O3 C24 C23 114.8(5) . . ?
C25 C24 C23 120.5(6) . . ?
C28 C27 C26 107.5(5) . . ?
C27 C28 N2 110.3(5) . . ?
C22 C23 C24 121.8(5) . . ?
C24 C25 C26 118.9(5) . . ?
C11 C12 C13 119.2(6) . . ?
C15 C16 C11 121.5(6) . . ?
C14 C13 C12 121.5(6) . . ?
C16 C15 C14 119.8(7) . . ?
C15 C14 C13 118.8(7) . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.047

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rm2131b_a
_database_code_depnum_ccdc_archive 'CCDC 2143129'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_rm2131b_a           
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.85 Report
RESPONSE: Highest residual electron density is present around H27
H27 was resolved using a DFIX command with 0.954 as distance lowering e denisty
The residual density is likely not from unaccounted atom types.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        N-phenyl-1H-indole-1-carboxamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.5956(4)
_cell_length_b                   23.7388(13)
_cell_length_c                   9.2195(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.725(7)
_cell_angle_gamma                90
_cell_volume                     1207.05(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    453(2)
_cell_measurement_reflns_used    2524
_cell_measurement_theta_min      4.0590
_cell_measurement_theta_max      28.3110

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      453(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6033
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.433
_diffrn_reflns_theta_max         29.740
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2867
_reflns_number_gt                2165
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelxle, ORTEP'
_computing_publication_material  publCIF
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0545P)²+0.3539P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2867
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7243(3) 0.26077(5) 0.58326(13) 0.0477(4) Uani 1 1 d . . . . .
N2 N 0.6853(3) 0.20837(6) 0.78508(16) 0.0388(4) Uani 1 1 d . . . . .
H2 H 0.673(4) 0.2137(8) 0.879(2) 0.047 Uiso 1 1 d . U . . .
N1 N 0.4878(3) 0.29333(6) 0.74520(16) 0.0371(3) Uani 1 1 d . . . . .
C17 C 0.6409(3) 0.25372(7) 0.69594(18) 0.0363(4) Uani 1 1 d . . . . .
C21 C 0.4838(3) 0.35142(7) 0.71569(18) 0.0344(4) Uani 1 1 d . . . . .
C11 C 0.8127(3) 0.16037(7) 0.74647(18) 0.0348(4) Uani 1 1 d . . . . .
C26 C 0.2977(3) 0.37482(7) 0.7812(2) 0.0385(4) Uani 1 1 d . . . . .
C22 C 0.6348(3) 0.38399(7) 0.64522(19) 0.0386(4) Uani 1 1 d . . . . .
H22 H 0.758321 0.367899 0.603124 0.046 Uiso 1 1 calc R U . . .
C12 C 1.0121(3) 0.14062(7) 0.8413(2) 0.0408(4) Uani 1 1 d . . . . .
H12 H 1.063530 0.158607 0.930746 0.049 Uiso 1 1 calc R U . . .
C23 C 0.5939(4) 0.44158(8) 0.6402(2) 0.0429(4) Uani 1 1 d . . . . .
H23 H 0.692100 0.464620 0.593606 0.051 Uiso 1 1 calc R U . . .
C16 C 0.7310(4) 0.13213(7) 0.6160(2) 0.0430(4) Uani 1 1 d . . . . .
H16 H 0.592713 0.144484 0.553654 0.052 Uiso 1 1 calc R U . . .
C25 C 0.2610(3) 0.43309(8) 0.7735(2) 0.0447(5) Uani 1 1 d . . . . .
H25 H 0.138097 0.449531 0.815407 0.054 Uiso 1 1 calc R U . . .
C24 C 0.4090(3) 0.46575(8) 0.7032(2) 0.0453(5) Uani 1 1 d . . . . .
H24 H 0.385451 0.504521 0.697610 0.054 Uiso 1 1 calc R U . . .
C15 C 0.8555(4) 0.08561(8) 0.5791(2) 0.0481(5) Uani 1 1 d . . . . .
H15 H 0.801785 0.066901 0.490992 0.058 Uiso 1 1 calc R U . . .
C14 C 1.0584(4) 0.06667(8) 0.6713(2) 0.0500(5) Uani 1 1 d . . . . .
H14 H 1.143366 0.035649 0.645173 0.060 Uiso 1 1 calc R U . . .
C28 C 0.3036(3) 0.28191(8) 0.8259(2) 0.0451(5) Uani 1 1 d . . . . .
C13 C 1.1351(4) 0.09396(8) 0.8028(2) 0.0503(5) Uani 1 1 d . . . . .
H13 H 1.270849 0.080873 0.866215 0.060 Uiso 1 1 calc R U . . .
C27 C 0.1847(3) 0.32968(8) 0.8486(3) 0.0487(5) Uani 1 1 d D . . . .
H27 H 0.047(3) 0.3262(9) 0.919(2) 0.058 Uiso 1 1 d D U . . .
H28 H 0.277(4) 0.2439(9) 0.855(2) 0.048(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.220(2) . ?
N2 C17 1.352(2) . ?
N2 C11 1.421(2) . ?
N2 H2 0.89(2) . ?
N1 C28 1.396(2) . ?
N1 C17 1.399(2) . ?
N1 C21 1.405(2) . ?
C21 C22 1.385(3) . ?
C21 C26 1.404(3) . ?
C11 C12 1.378(2) . ?
C11 C16 1.385(2) . ?
C26 C25 1.399(2) . ?
C26 C27 1.437(3) . ?
C22 C23 1.386(2) . ?
C22 H22 0.9300 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C23 C24 1.393(3) . ?
C23 H23 0.9300 . ?
C16 C15 1.379(3) . ?
C16 H16 0.9300 . ?
C25 C24 1.374(3) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
C15 C14 1.374(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.378(3) . ?
C14 H14 0.9300 . ?
C28 C27 1.349(3) . ?
C28 H28 0.96(2) . ?
C13 H13 0.9300 . ?
C27 H27 1.086(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N2 C11 122.33(15) . . ?
C17 N2 H2 116.2(13) . . ?
C11 N2 H2 118.9(13) . . ?
C28 N1 C17 126.20(14) . . ?
C28 N1 C21 107.76(15) . . ?
C17 N1 C21 125.97(15) . . ?
O1 C17 N2 124.73(16) . . ?
O1 C17 N1 121.83(15) . . ?
N2 C17 N1 113.43(15) . . ?
C22 C21 C26 122.45(16) . . ?
C22 C21 N1 130.37(16) . . ?
C26 C21 N1 107.07(15) . . ?
C12 C11 C16 119.95(16) . . ?
C12 C11 N2 120.03(15) . . ?
C16 C11 N2 119.98(15) . . ?
C25 C26 C21 118.86(17) . . ?
C25 C26 C27 133.46(18) . . ?
C21 C26 C27 107.67(15) . . ?
C21 C22 C23 117.14(17) . . ?
C21 C22 H22 121.4 . . ?
C23 C22 H22 121.4 . . ?
C11 C12 C13 119.66(17) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C22 C23 C24 121.50(18) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C15 C16 C11 119.70(17) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C24 C25 C26 119.15(18) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C24 C23 120.90(17) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C14 C15 C16 120.57(18) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C14 C13 119.52(18) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C27 C28 N1 110.33(17) . . ?
C27 C28 H28 130.1(12) . . ?
N1 C28 H28 119.6(12) . . ?
C14 C13 C12 120.55(18) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C28 C27 C26 107.17(18) . . ?
C28 C27 H27 116.4(11) . . ?
C26 C27 H27 136.1(11) . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042




_publcif_funding_html            
;
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rm2143_a
_database_code_depnum_ccdc_archive 'CCDC 2125086'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_rm2143_a            
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         13 Note  
RESPONSE: A small number of low angle reflections (14) were obscured by the beamstop.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H13 B Cl F15 N2 O'
_chemical_formula_sum            'C34 H13 B Cl F15 N2 O'
_chemical_formula_weight         796.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0666(6)
_cell_length_b                   12.7868(8)
_cell_length_c                   15.6641(11)
_cell_angle_alpha                77.581(6)
_cell_angle_beta                 87.401(6)
_cell_angle_gamma                78.419(6)
_cell_volume                     1545.76(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5674
_cell_measurement_theta_min      3.6830
_cell_measurement_theta_max      29.5370

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.197
_exptl_absorpt_coefficient_mu    0.249
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15105
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.327
_diffrn_reflns_theta_max         29.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7363
_reflns_number_gt                5314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    gaussian
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.9717P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7363
_refine_ls_number_parameters     492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.32726(9) 0.84011(5) 0.33201(5) 0.0592(2) Uani 1 1 d . . . . .
F35 F -0.02070(14) 0.47907(9) 0.17359(7) 0.0298(3) Uani 1 1 d . . . . .
F51 F 0.30835(15) 0.43974(9) 0.12262(8) 0.0339(3) Uani 1 1 d . . . . .
F31 F 0.27696(15) 0.42258(10) 0.43984(8) 0.0363(3) Uani 1 1 d . . . . .
F41 F -0.06957(14) 0.27292(10) 0.34389(8) 0.0394(3) Uani 1 1 d . . . . .
F34 F -0.15875(15) 0.67941(10) 0.19237(9) 0.0401(3) Uani 1 1 d . . . . .
F45 F 0.49912(14) 0.17871(10) 0.44065(9) 0.0404(3) Uani 1 1 d . . . . .
F55 F 0.1748(2) 0.10272(10) 0.27241(8) 0.0472(4) Uani 1 1 d . . . . .
F43 F 0.07884(18) 0.03044(11) 0.61125(8) 0.0466(3) Uani 1 1 d . . . . .
O1 O 0.43773(16) 0.33956(11) 0.30170(9) 0.0259(3) Uani 1 1 d . . . . .
F44 F 0.40719(18) 0.04938(11) 0.58298(9) 0.0474(3) Uani 1 1 d . . . . .
F42 F -0.15920(16) 0.14228(11) 0.48798(9) 0.0476(4) Uani 1 1 d . . . . .
F33 F -0.09799(18) 0.75094(10) 0.33681(10) 0.0512(4) Uani 1 1 d . . . . .
F54 F 0.2001(2) 0.03488(11) 0.12450(9) 0.0527(4) Uani 1 1 d . . . . .
F32 F 0.12069(18) 0.61815(11) 0.46122(9) 0.0477(4) Uani 1 1 d . . . . .
F52 F 0.32064(19) 0.37178(12) -0.02665(8) 0.0517(4) Uani 1 1 d . . . . .
F53 F 0.2775(2) 0.16538(12) -0.02734(9) 0.0547(4) Uani 1 1 d . . . . .
N1 N 0.6427(2) 0.42034(14) 0.23729(12) 0.0316(4) Uani 1 1 d . . . . .
H1 H 0.742722 0.414668 0.211885 0.038 Uiso 1 1 calc R U . . .
N2 N 0.6838(2) 0.07567(14) 0.18575(12) 0.0331(4) Uani 1 1 d . . . . .
C40 C 0.2185(2) 0.23310(15) 0.38503(12) 0.0229(4) Uani 1 1 d . . . . .
C30 C 0.1432(2) 0.44055(15) 0.30377(12) 0.0236(4) Uani 1 1 d . . . . .
C35 C 0.0266(2) 0.51060(15) 0.24536(12) 0.0243(4) Uani 1 1 d . . . . .
C10 C 0.5671(2) 0.33518(15) 0.25070(12) 0.0248(4) Uani 1 1 d . . . . .
C31 C 0.1691(2) 0.48280(16) 0.37597(13) 0.0270(4) Uani 1 1 d . . . . .
C50 C 0.2364(2) 0.27738(15) 0.20611(13) 0.0257(4) Uani 1 1 d . . . . .
C45 C 0.3334(2) 0.17339(16) 0.44855(13) 0.0272(4) Uani 1 1 d . . . . .
C34 C -0.0516(2) 0.61444(16) 0.25396(14) 0.0286(4) Uani 1 1 d . . . . .
C41 C 0.0527(2) 0.21899(16) 0.40288(13) 0.0273(4) Uani 1 1 d . . . . .
C11 C 0.5686(2) 0.52210(16) 0.26242(14) 0.0281(4) Uani 1 1 d . . . . .
C21 C 0.7209(2) 0.24751(16) 0.12678(13) 0.0269(4) Uani 1 1 d . . . . .
C20 C 0.6328(2) 0.24561(16) 0.20959(13) 0.0268(4) Uani 1 1 d . . . . .
C51 C 0.2725(2) 0.33962(16) 0.12578(13) 0.0273(4) Uani 1 1 d . . . . .
C26 C 0.7484(2) 0.13954(16) 0.11399(13) 0.0300(4) Uani 1 1 d . . . . .
C42 C 0.0033(2) 0.15213(17) 0.47630(14) 0.0302(4) Uani 1 1 d . . . . .
C43 C 0.1228(3) 0.09521(16) 0.53762(13) 0.0321(5) Uani 1 1 d . . . . .
C44 C 0.2887(3) 0.10512(16) 0.52330(13) 0.0304(4) Uani 1 1 d . . . . .
C55 C 0.2091(3) 0.17485(16) 0.20081(13) 0.0302(4) Uani 1 1 d . . . . .
C33 C -0.0200(3) 0.65125(16) 0.32664(15) 0.0328(5) Uani 1 1 d . . . . .
C32 C 0.0902(3) 0.58436(17) 0.38865(14) 0.0325(5) Uani 1 1 d . . . . .
C22 C 0.7693(3) 0.32794(18) 0.06059(14) 0.0350(5) Uani 1 1 d . . . . .
H22 H 0.750328 0.401768 0.066629 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4741(3) 0.60344(17) 0.20127(14) 0.0323(5) Uani 1 1 d . . . . .
H12 H 0.458860 0.591959 0.144430 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4014(3) 0.70185(18) 0.22304(15) 0.0362(5) Uani 1 1 d . . . . .
H13 H 0.336437 0.758448 0.181240 0.043 Uiso 1 1 calc R U . . .
C27 C 0.6148(3) 0.13936(17) 0.24151(14) 0.0308(4) Uani 1 1 d . . . . .
C52 C 0.2840(3) 0.30569(19) 0.04799(13) 0.0340(5) Uani 1 1 d . . . . .
C53 C 0.2612(3) 0.20196(19) 0.04767(14) 0.0369(5) Uani 1 1 d . . . . .
C14 C 0.4241(3) 0.71712(18) 0.30565(15) 0.0353(5) Uani 1 1 d . . . . .
C54 C 0.2225(3) 0.13664(17) 0.12394(15) 0.0352(5) Uani 1 1 d . . . . .
C25 C 0.8232(3) 0.10955(19) 0.03856(14) 0.0366(5) Uani 1 1 d . . . . .
H25 H 0.839900 0.036372 0.031096 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5189(3) 0.6361(2) 0.36731(15) 0.0408(5) Uani 1 1 d . . . . .
H15 H 0.533720 0.647825 0.424110 0.049 Uiso 1 1 calc R U . . .
C16 C 0.5923(3) 0.53739(18) 0.34537(15) 0.0363(5) Uani 1 1 d . . . . .
H16 H 0.658037 0.480951 0.386984 0.044 Uiso 1 1 calc R U . . .
C24 C 0.8717(3) 0.1905(2) -0.02448(15) 0.0404(5) Uani 1 1 d . . . . .
H24 H 0.924239 0.172819 -0.076425 0.048 Uiso 1 1 calc R U . . .
C23 C 0.8453(3) 0.2983(2) -0.01383(15) 0.0414(5) Uani 1 1 d . . . . .
H23 H 0.880271 0.352365 -0.058675 0.050 Uiso 1 1 calc R U . . .
B1 B 0.2554(3) 0.31894(17) 0.29677(14) 0.0228(4) Uani 1 1 d . . . . .
C28 C 0.6917(4) -0.04159(19) 0.19814(18) 0.0568(7) Uani 1 1 d . . . . .
H28A H 0.637819 -0.067931 0.253782 0.085 Uiso 1 1 calc R U . . .
H28B H 0.810275 -0.079272 0.198839 0.085 Uiso 1 1 calc R U . . .
H28C H 0.632415 -0.056357 0.150117 0.085 Uiso 1 1 calc R U . . .
H27 H 0.567(3) 0.1094(18) 0.2933(16) 0.036(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.735(2) . ?
F35 C35 1.366(2) . ?
F51 C51 1.358(2) . ?
F31 C31 1.353(2) . ?
F41 C41 1.355(2) . ?
F34 C34 1.346(2) . ?
F45 C45 1.351(2) . ?
F55 C55 1.347(2) . ?
F43 C43 1.346(2) . ?
O1 C10 1.285(2) . ?
O1 B1 1.554(2) . ?
F44 C44 1.348(2) . ?
F42 C42 1.342(2) . ?
F33 C33 1.343(2) . ?
F54 C54 1.347(2) . ?
F32 C32 1.349(2) . ?
F52 C52 1.346(2) . ?
F53 C53 1.347(2) . ?
N1 C10 1.326(2) . ?
N1 C11 1.446(2) . ?
N2 C27 1.347(3) . ?
N2 C26 1.388(3) . ?
N2 C28 1.459(3) . ?
C40 C45 1.381(3) . ?
C40 C41 1.393(3) . ?
C40 B1 1.627(3) . ?
C30 C35 1.383(3) . ?
C30 C31 1.394(3) . ?
C30 B1 1.658(3) . ?
C35 C34 1.383(3) . ?
C10 C20 1.432(3) . ?
C31 C32 1.378(3) . ?
C50 C51 1.390(3) . ?
C50 C55 1.392(3) . ?
C50 B1 1.643(3) . ?
C45 C44 1.383(3) . ?
C34 C33 1.374(3) . ?
C41 C42 1.373(3) . ?
C11 C12 1.378(3) . ?
C11 C16 1.382(3) . ?
C21 C22 1.397(3) . ?
C21 C26 1.410(3) . ?
C21 C20 1.448(3) . ?
C20 C27 1.377(3) . ?
C51 C52 1.372(3) . ?
C26 C25 1.394(3) . ?
C42 C43 1.372(3) . ?
C43 C44 1.373(3) . ?
C55 C54 1.386(3) . ?
C33 C32 1.371(3) . ?
C22 C23 1.382(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.375(3) . ?
C52 C53 1.376(3) . ?
C53 C54 1.365(3) . ?
C14 C15 1.382(3) . ?
C25 C24 1.374(3) . ?
C15 C16 1.389(3) . ?
C24 C23 1.396(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 B1 134.59(15) . . ?
C10 N1 C11 123.13(16) . . ?
C27 N2 C26 108.95(17) . . ?
C27 N2 C28 126.14(19) . . ?
C26 N2 C28 124.90(18) . . ?
C45 C40 C41 114.13(17) . . ?
C45 C40 B1 127.32(16) . . ?
C41 C40 B1 118.50(17) . . ?
C35 C30 C31 113.14(17) . . ?
C35 C30 B1 128.78(17) . . ?
C31 C30 B1 118.05(17) . . ?
F35 C35 C34 115.06(17) . . ?
F35 C35 C30 120.55(16) . . ?
C34 C35 C30 124.40(18) . . ?
O1 C10 N1 116.04(17) . . ?
O1 C10 C20 124.46(17) . . ?
N1 C10 C20 119.49(17) . . ?
F31 C31 C32 115.57(17) . . ?
F31 C31 C30 119.99(17) . . ?
C32 C31 C30 124.43(18) . . ?
C51 C50 C55 113.23(17) . . ?
C51 C50 B1 120.38(16) . . ?
C55 C50 B1 125.76(17) . . ?
F45 C45 C40 121.08(17) . . ?
F45 C45 C44 115.78(17) . . ?
C40 C45 C44 123.15(18) . . ?
F34 C34 C33 119.73(18) . . ?
F34 C34 C35 120.82(18) . . ?
C33 C34 C35 119.45(18) . . ?
F41 C41 C42 116.81(17) . . ?
F41 C41 C40 118.73(17) . . ?
C42 C41 C40 124.45(18) . . ?
C12 C11 C16 120.96(19) . . ?
C12 C11 N1 118.14(18) . . ?
C16 C11 N1 120.90(19) . . ?
C22 C21 C26 118.46(19) . . ?
C22 C21 C20 135.67(19) . . ?
C26 C21 C20 105.70(17) . . ?
C27 C20 C10 124.85(18) . . ?
C27 C20 C21 106.70(17) . . ?
C10 C20 C21 128.38(17) . . ?
F51 C51 C52 115.99(18) . . ?
F51 C51 C50 118.98(17) . . ?
C52 C51 C50 124.93(19) . . ?
N2 C26 C25 128.89(19) . . ?
N2 C26 C21 108.24(17) . . ?
C25 C26 C21 122.83(19) . . ?
F42 C42 C41 120.63(19) . . ?
F42 C42 C43 120.43(18) . . ?
C41 C42 C43 118.94(18) . . ?
F43 C43 C42 120.71(19) . . ?
F43 C43 C44 120.0(2) . . ?
C42 C43 C44 119.27(18) . . ?
F44 C44 C43 119.75(18) . . ?
F44 C44 C45 120.19(18) . . ?
C43 C44 C45 120.05(19) . . ?
F55 C55 C54 114.74(18) . . ?
F55 C55 C50 121.52(17) . . ?
C54 C55 C50 123.7(2) . . ?
F33 C33 C34 120.07(19) . . ?
F33 C33 C32 120.83(19) . . ?
C34 C33 C32 119.09(18) . . ?
F32 C32 C33 120.05(18) . . ?
F32 C32 C31 120.55(19) . . ?
C33 C32 C31 119.41(18) . . ?
C23 C22 C21 118.9(2) . . ?
C11 C12 C13 119.7(2) . . ?
C14 C13 C12 119.5(2) . . ?
N2 C27 C20 110.39(19) . . ?
F52 C52 C51 120.6(2) . . ?
F52 C52 C53 120.38(19) . . ?
C51 C52 C53 119.0(2) . . ?
F53 C53 C54 120.5(2) . . ?
F53 C53 C52 120.1(2) . . ?
C54 C53 C52 119.44(19) . . ?
C13 C14 C15 121.2(2) . . ?
C13 C14 Cl1 118.50(18) . . ?
C15 C14 Cl1 120.28(17) . . ?
F54 C54 C53 120.00(19) . . ?
F54 C54 C55 120.3(2) . . ?
C53 C54 C55 119.7(2) . . ?
C24 C25 C26 117.1(2) . . ?
C14 C15 C16 119.3(2) . . ?
C11 C16 C15 119.3(2) . . ?
C25 C24 C23 121.4(2) . . ?
C22 C23 C24 121.4(2) . . ?
O1 B1 C40 108.68(15) . . ?
O1 B1 C50 108.85(15) . . ?
C40 B1 C50 113.88(15) . . ?
O1 B1 C30 100.41(14) . . ?
C40 B1 C30 107.28(15) . . ?
C50 B1 C30 116.71(16) . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.052

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rm2144_a
_database_code_depnum_ccdc_archive 'CCDC 2125087'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_rm2144_a            
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         13 Note  
RESPONSE: A small number of low angle reflections (13) were obscured by the beamstop.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H14 B F15 N2 O'
_chemical_formula_sum            'C34 H14 B F15 N2 O'
_chemical_formula_weight         762.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9694(4)
_cell_length_b                   12.4723(8)
_cell_length_c                   15.5816(8)
_cell_angle_alpha                78.311(5)
_cell_angle_beta                 86.618(4)
_cell_angle_gamma                79.065(4)
_cell_volume                     1488.76(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5110
_cell_measurement_theta_min      3.7490
_cell_measurement_theta_max      28.5490

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.167
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13554
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.393
_diffrn_reflns_theta_max         29.859
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7125
_reflns_number_gt                5067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    mercury
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.5895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7125
_refine_ls_number_parameters     483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F31 F 0.68391(13) 0.56644(9) 0.87338(7) 0.0297(3) Uani 1 1 d . . . . .
F51 F 0.74734(14) 0.57159(9) 0.55521(7) 0.0332(3) Uani 1 1 d . . . . .
F55 F 1.01860(13) 0.52909(9) 0.82640(7) 0.0289(2) Uani 1 1 d . . . . .
F41 F 1.07357(13) 0.73687(10) 0.64160(8) 0.0365(3) Uani 1 1 d . . . . .
F45 F 0.49352(13) 0.81821(9) 0.55952(7) 0.0346(3) Uani 1 1 d . . . . .
F54 F 1.15688(14) 0.32233(9) 0.81400(8) 0.0396(3) Uani 1 1 d . . . . .
F44 F 0.57462(15) 0.94712(10) 0.41324(8) 0.0401(3) Uani 1 1 d . . . . .
F42 F 1.15235(14) 0.86695(10) 0.49159(8) 0.0417(3) Uani 1 1 d . . . . .
F52 F 0.90362(16) 0.36965(10) 0.54060(8) 0.0427(3) Uani 1 1 d . . . . .
F35 F 0.82680(18) 0.90748(10) 0.72050(8) 0.0460(3) Uani 1 1 d . . . . .
O1 O 0.56785(15) 0.65479(10) 0.69346(8) 0.0239(3) Uani 1 1 d . . . . .
F32 F 0.66781(17) 0.64159(11) 1.02224(8) 0.0464(3) Uani 1 1 d . . . . .
F43 F 0.90272(17) 0.97605(10) 0.37655(8) 0.0436(3) Uani 1 1 d . . . . .
F34 F 0.80548(18) 0.97994(10) 0.86838(9) 0.0496(3) Uani 1 1 d . . . . .
F53 F 1.10661(17) 0.23946(10) 0.67159(9) 0.0502(4) Uani 1 1 d . . . . .
F33 F 0.72105(18) 0.85131(11) 1.02154(8) 0.0505(3) Uani 1 1 d . . . . .
N2 N 0.37060(19) 0.56169(13) 0.75919(11) 0.0304(4) Uani 1 1 d . . . . .
H2 H 0.272918 0.562121 0.788678 0.036 Uiso 1 1 calc R U . . .
N1 N 0.3152(2) 0.91569(13) 0.81593(11) 0.0304(4) Uani 1 1 d . . . . .
C40 C 0.7803(2) 0.77073(14) 0.60886(12) 0.0224(4) Uani 1 1 d . . . . .
C45 C 0.6602(2) 0.82747(15) 0.54745(12) 0.0248(4) Uani 1 1 d . . . . .
C10 C 0.4386(2) 0.65260(15) 0.74629(12) 0.0232(4) Uani 1 1 d . . . . .
C11 C 0.3664(2) 0.74260(15) 0.78939(12) 0.0253(4) Uani 1 1 d . . . . .
C44 C 0.6987(2) 0.89600(15) 0.47075(12) 0.0274(4) Uani 1 1 d . . . . .
C50 C 0.8674(2) 0.56145(14) 0.69315(12) 0.0231(4) Uani 1 1 d . . . . .
C51 C 0.8490(2) 0.51372(15) 0.62148(12) 0.0256(4) Uani 1 1 d . . . . .
C13 C 0.2515(2) 0.84962(15) 0.88826(12) 0.0273(4) Uani 1 1 d . . . . .
C41 C 0.9458(2) 0.78839(15) 0.58595(13) 0.0264(4) Uani 1 1 d . . . . .
C42 C 0.9890(2) 0.85539(16) 0.50987(13) 0.0295(4) Uani 1 1 d . . . . .
C18 C 0.2792(2) 0.73952(15) 0.87399(12) 0.0254(4) Uani 1 1 d . . . . .
C55 C 0.9782(2) 0.49281(15) 0.75472(12) 0.0233(4) Uani 1 1 d . . . . .
C54 C 1.0561(2) 0.38545(15) 0.74961(13) 0.0278(4) Uani 1 1 d . . . . .
C30 C 0.7613(2) 0.73001(15) 0.78833(12) 0.0237(4) Uani 1 1 d . . . . .
C20 C 0.4468(2) 0.46161(16) 0.72781(13) 0.0284(4) Uani 1 1 d . . . . .
C43 C 0.8643(3) 0.91026(15) 0.45187(12) 0.0294(4) Uani 1 1 d . . . . .
C31 C 0.7218(2) 0.66909(15) 0.86921(12) 0.0253(4) Uani 1 1 d . . . . .
C52 C 0.9283(2) 0.40846(16) 0.61216(13) 0.0297(4) Uani 1 1 d . . . . .
C32 C 0.7100(2) 0.70602(17) 0.94706(13) 0.0311(4) Uani 1 1 d . . . . .
C35 C 0.7907(2) 0.83503(16) 0.79317(13) 0.0294(4) Uani 1 1 d . . . . .
C12 C 0.3838(2) 0.85142(16) 0.75841(13) 0.0287(4) Uani 1 1 d . . . . .
C17 C 0.2313(2) 0.65683(17) 0.94010(14) 0.0328(5) Uani 1 1 d . . . . .
H17 H 0.250288 0.581552 0.933048 0.039 Uiso 1 1 calc R U . . .
C53 C 1.0309(2) 0.34344(15) 0.67751(14) 0.0322(5) Uani 1 1 d . . . . .
C34 C 0.7794(3) 0.87598(16) 0.86967(14) 0.0332(5) Uani 1 1 d . . . . .
C14 C 0.1773(3) 0.87931(17) 0.96528(13) 0.0339(5) Uani 1 1 d . . . . .
H14 H 0.160400 0.953991 0.973683 0.041 Uiso 1 1 calc R U . . .
C33 C 0.7371(3) 0.81140(18) 0.94710(13) 0.0346(5) Uani 1 1 d . . . . .
C25 C 0.4217(3) 0.45260(18) 0.64280(14) 0.0360(5) Uani 1 1 d . . . . .
H25 H 0.356184 0.512562 0.604032 0.043 Uiso 1 1 calc R U . . .
C16 C 0.1562(3) 0.68629(18) 1.01572(14) 0.0389(5) Uani 1 1 d . . . . .
H16 H 0.121323 0.630522 1.060558 0.047 Uiso 1 1 calc R U . . .
C21 C 0.5411(3) 0.37491(17) 0.78490(14) 0.0355(5) Uani 1 1 d . . . . .
H21 H 0.557766 0.381879 0.843252 0.043 Uiso 1 1 calc R U . . .
C22 C 0.6112(3) 0.27739(18) 0.75603(16) 0.0421(5) Uani 1 1 d . . . . .
H22 H 0.675946 0.217071 0.794789 0.051 Uiso 1 1 calc R U . . .
C23 C 0.5869(3) 0.26803(18) 0.67124(16) 0.0422(5) Uani 1 1 d . . . . .
H23 H 0.635162 0.201211 0.651699 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1297(3) 0.79620(19) 1.02841(14) 0.0384(5) Uani 1 1 d . . . . .
H15 H 0.077937 0.813481 1.081626 0.046 Uiso 1 1 calc R U . . .
C24 C 0.4932(3) 0.35490(19) 0.61475(16) 0.0433(5) Uani 1 1 d . . . . .
H24 H 0.477388 0.347977 0.556296 0.052 Uiso 1 1 calc R U . . .
B1 B 0.7478(3) 0.68353(17) 0.69850(14) 0.0222(4) Uani 1 1 d . . . . .
C19 C 0.3121(4) 1.03456(17) 0.80639(16) 0.0511(6) Uani 1 1 d . . . . .
H19A H 0.364023 1.062574 0.749698 0.077 Uiso 1 1 calc R U . . .
H19B H 0.376593 1.047715 0.853704 0.077 Uiso 1 1 calc R U . . .
H19C H 0.193505 1.073454 0.809348 0.077 Uiso 1 1 calc R U . . .
H1 H 0.434(2) 0.8856(17) 0.7042(14) 0.031(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F31 C31 1.359(2) . ?
F51 C51 1.348(2) . ?
F55 C55 1.363(2) . ?
F41 C41 1.353(2) . ?
F45 C45 1.354(2) . ?
F54 C54 1.344(2) . ?
F44 C44 1.350(2) . ?
F42 C42 1.344(2) . ?
F52 C52 1.340(2) . ?
F35 C35 1.352(2) . ?
O1 C10 1.281(2) . ?
O1 B1 1.553(2) . ?
F32 C32 1.344(2) . ?
F43 C43 1.344(2) . ?
F34 C34 1.348(2) . ?
F53 C53 1.341(2) . ?
F33 C33 1.342(2) . ?
N2 C10 1.322(2) . ?
N2 C20 1.446(2) . ?
N1 C12 1.346(2) . ?
N1 C13 1.386(2) . ?
N1 C19 1.455(3) . ?
C40 C45 1.382(2) . ?
C40 C41 1.393(2) . ?
C40 B1 1.628(3) . ?
C45 C44 1.377(3) . ?
C10 C11 1.434(3) . ?
C11 C12 1.376(3) . ?
C11 C18 1.450(3) . ?
C44 C43 1.372(3) . ?
C50 C55 1.383(2) . ?
C50 C51 1.395(3) . ?
C50 B1 1.651(3) . ?
C51 C52 1.377(3) . ?
C13 C14 1.393(3) . ?
C13 C18 1.410(3) . ?
C41 C42 1.372(3) . ?
C42 C43 1.368(3) . ?
C18 C17 1.394(3) . ?
C55 C54 1.381(3) . ?
C54 C53 1.372(3) . ?
C30 C31 1.386(3) . ?
C30 C35 1.391(3) . ?
C30 B1 1.636(3) . ?
C20 C21 1.381(3) . ?
C20 C25 1.381(3) . ?
C31 C32 1.374(3) . ?
C52 C53 1.370(3) . ?
C32 C33 1.372(3) . ?
C35 C34 1.381(3) . ?
C17 C16 1.375(3) . ?
C34 C33 1.371(3) . ?
C14 C15 1.370(3) . ?
C25 C24 1.387(3) . ?
C16 C15 1.399(3) . ?
C21 C22 1.389(3) . ?
C22 C23 1.378(3) . ?
C23 C24 1.375(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 B1 133.76(15) . . ?
C10 N2 C20 124.03(15) . . ?
C12 N1 C13 108.93(16) . . ?
C12 N1 C19 126.32(17) . . ?
C13 N1 C19 124.72(17) . . ?
C45 C40 C41 113.79(16) . . ?
C45 C40 B1 126.85(16) . . ?
C41 C40 B1 119.25(15) . . ?
F45 C45 C44 115.27(15) . . ?
F45 C45 C40 121.09(16) . . ?
C44 C45 C40 123.64(17) . . ?
O1 C10 N2 116.30(16) . . ?
O1 C10 C11 123.47(16) . . ?
N2 C10 C11 120.22(16) . . ?
C12 C11 C10 123.81(18) . . ?
C12 C11 C18 106.54(17) . . ?
C10 C11 C18 129.41(17) . . ?
F44 C44 C43 119.96(16) . . ?
F44 C44 C45 120.15(17) . . ?
C43 C44 C45 119.87(17) . . ?
C55 C50 C51 113.06(16) . . ?
C55 C50 B1 128.57(17) . . ?
C51 C50 B1 118.16(15) . . ?
F51 C51 C52 115.51(17) . . ?
F51 C51 C50 119.90(16) . . ?
C52 C51 C50 124.59(17) . . ?
N1 C13 C14 128.93(18) . . ?
N1 C13 C18 108.25(16) . . ?
C14 C13 C18 122.79(18) . . ?
F41 C41 C42 117.18(16) . . ?
F41 C41 C40 118.69(16) . . ?
C42 C41 C40 124.13(17) . . ?
F42 C42 C43 119.83(17) . . ?
F42 C42 C41 120.72(17) . . ?
C43 C42 C41 119.45(17) . . ?
C17 C18 C13 118.51(18) . . ?
C17 C18 C11 135.67(18) . . ?
C13 C18 C11 105.68(16) . . ?
F55 C55 C54 114.96(16) . . ?
F55 C55 C50 120.69(16) . . ?
C54 C55 C50 124.35(18) . . ?
F54 C54 C53 119.86(17) . . ?
F54 C54 C55 120.78(18) . . ?
C53 C54 C55 119.36(17) . . ?
C31 C30 C35 112.80(17) . . ?
C31 C30 B1 120.60(16) . . ?
C35 C30 B1 126.16(16) . . ?
C21 C20 C25 120.99(19) . . ?
C21 C20 N2 118.78(18) . . ?
C25 C20 N2 120.21(18) . . ?
F43 C43 C42 120.83(17) . . ?
F43 C43 C44 120.05(17) . . ?
C42 C43 C44 119.11(17) . . ?
F31 C31 C32 115.92(16) . . ?
F31 C31 C30 118.88(16) . . ?
C32 C31 C30 125.13(17) . . ?
F52 C52 C53 120.47(17) . . ?
F52 C52 C51 120.44(17) . . ?
C53 C52 C51 119.09(18) . . ?
F32 C32 C33 119.87(18) . . ?
F32 C32 C31 120.92(18) . . ?
C33 C32 C31 119.18(18) . . ?
F35 C35 C34 114.51(17) . . ?
F35 C35 C30 121.27(17) . . ?
C34 C35 C30 124.17(18) . . ?
N1 C12 C11 110.59(18) . . ?
C16 C17 C18 118.74(19) . . ?
F53 C53 C52 120.64(19) . . ?
F53 C53 C54 119.91(18) . . ?
C52 C53 C54 119.44(17) . . ?
F34 C34 C33 119.78(18) . . ?
F34 C34 C35 120.47(18) . . ?
C33 C34 C35 119.72(18) . . ?
C15 C14 C13 117.15(19) . . ?
F33 C33 C34 120.35(19) . . ?
F33 C33 C32 120.67(19) . . ?
C34 C33 C32 118.98(18) . . ?
C20 C25 C24 119.2(2) . . ?
C17 C16 C15 121.8(2) . . ?
C20 C21 C22 119.2(2) . . ?
C23 C22 C21 120.1(2) . . ?
C24 C23 C22 120.3(2) . . ?
C14 C15 C16 121.0(2) . . ?
C23 C24 C25 120.2(2) . . ?
O1 B1 C40 107.59(14) . . ?
O1 B1 C30 109.95(14) . . ?
C40 B1 C30 114.14(15) . . ?
O1 B1 C50 99.70(13) . . ?
C40 B1 C50 108.18(15) . . ?
C30 B1 C50 116.05(15) . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rm2217b_a
_database_code_depnum_ccdc_archive 'CCDC 2163368'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2022-03-30 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 B Cl3 N'
_chemical_formula_sum            'C8 H7 B Cl3 N'
_chemical_formula_weight         234.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.121(2)
_cell_length_b                   6.9264(7)
_cell_length_c                   9.8879(13)
_cell_angle_alpha                90
_cell_angle_beta                 109.906(14)
_cell_angle_gamma                90
_cell_volume                     973.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    1123
_cell_measurement_theta_min      4.1260
_cell_measurement_theta_max      28.3460

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.146
_exptl_absorpt_coefficient_mu    0.886
_shelx_estimated_absorpt_T_min   0.603
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2544
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.657
_diffrn_reflns_theta_max         29.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1257
_reflns_number_gt                1018
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL, ORTEP, mercury'
_computing_publication_material  publCIF
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+0.6801P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1257
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.8267(2) 0.500000 0.6896(3) 0.0203(6) Uani 1 2 d S T P . .
C4 C 0.7317(2) 0.500000 0.6753(3) 0.0184(6) Uani 1 2 d S T P . .
C5 C 0.6599(2) 0.500000 0.5443(3) 0.0225(6) Uani 1 2 d S T P . .
H5 H 0.595670 0.500000 0.537228 0.027 Uiso 1 2 calc R U P . .
C6 C 0.6865(2) 0.500000 0.4232(3) 0.0264(7) Uani 1 2 d S T P . .
H6 H 0.639438 0.500000 0.330542 0.032 Uiso 1 2 calc R U P . .
C8 C 0.8517(2) 0.500000 0.5674(3) 0.0262(7) Uani 1 2 d S T P . .
H8 H 0.915923 0.500000 0.574541 0.031 Uiso 1 2 calc R U P . .
C7 C 0.7811(2) 0.500000 0.4348(3) 0.0274(7) Uani 1 2 d S T P . .
H7 H 0.797223 0.500000 0.349977 0.033 Uiso 1 2 calc R U P . .
Cl1 Cl 0.56507(4) 0.72003(8) 0.76832(6) 0.03092(18) Uani 1 1 d . . . . .
N1 N 0.72512(16) 0.500000 0.8176(2) 0.0185(5) Uani 1 2 d S T P . .
C1 C 0.8086(2) 0.500000 0.9123(3) 0.0239(6) Uani 1 2 d S T P . .
H1 H 0.820950 0.500000 1.013119 0.029 Uiso 1 2 calc R U P . .
B1 B 0.6299(2) 0.500000 0.8490(4) 0.0217(7) Uani 1 2 d S T P . .
Cl2 Cl 0.65529(6) 0.500000 1.04463(8) 0.0329(2) Uani 1 2 d S T P . .
C2 C 0.8830(2) 0.500000 0.8460(3) 0.0246(7) Uani 1 2 d S T P . .
H2A H 0.923049 0.383463 0.873425 0.030 Uiso 0.5 1 calc R U P . .
H2B H 0.923049 0.616537 0.873426 0.030 Uiso 0.5 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C8 1.383(4) . ?
C3 C4 1.396(4) . ?
C3 C2 1.490(4) . ?
C4 C5 1.378(4) . ?
C4 N1 1.443(3) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C8 C7 1.380(4) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
Cl1 B1 1.840(2) . ?
N1 C1 1.290(4) . ?
N1 B1 1.573(4) . ?
C1 C2 1.483(4) . ?
C1 H1 0.9500 . ?
B1 Cl2 1.840(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C3 C4 119.3(3) . . ?
C8 C3 C2 132.7(3) . . ?
C4 C3 C2 108.0(2) . . ?
C5 C4 C3 123.3(3) . . ?
C5 C4 N1 128.6(3) . . ?
C3 C4 N1 108.1(2) . . ?
C4 C5 C6 116.4(3) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C7 C8 C3 118.5(3) . . ?
C7 C8 H8 120.7 . . ?
C3 C8 H8 120.7 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C1 N1 C4 109.4(2) . . ?
C1 N1 B1 126.3(2) . . ?
C4 N1 B1 124.3(2) . . ?
N1 C1 C2 112.4(3) . . ?
N1 C1 H1 123.8 . . ?
C2 C1 H1 123.8 . . ?
N1 B1 Cl2 109.3(2) . . ?
N1 B1 Cl1 107.62(13) . . ?
Cl2 B1 Cl1 110.21(11) . . ?
N1 B1 Cl1 107.62(13) . 6_565 ?
Cl2 B1 Cl1 110.21(11) . 6_565 ?
Cl1 B1 Cl1 111.80(18) . 6_565 ?
C1 C2 C3 102.0(2) . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2B 111.4 . . ?
C3 C2 H2B 111.4 . . ?
H2A C2 H2B 109.2 . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.066




_publcif_funding_html            
;
;
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rm2142_a
_database_code_depnum_ccdc_archive 'CCDC 2125085'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H16 B Br Cl2 F10 N3 O2, C H2 Cl2'
_chemical_formula_sum            'C36 H17 B Br Cl4 F10 N3 O2'
_chemical_formula_weight         946.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.7275(4)
_cell_length_b                   16.2624(4)
_cell_length_c                   19.5564(6)
_cell_angle_alpha                69.141(3)
_cell_angle_beta                 77.001(3)
_cell_angle_gamma                87.734(2)
_cell_volume                     3681.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    13561
_cell_measurement_theta_min      3.7940
_cell_measurement_theta_max      72.9710

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.047
_exptl_absorpt_coefficient_mu    5.014
_shelx_estimated_absorpt_T_min   0.286
_shelx_estimated_absorpt_T_max   0.798
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26747
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.567
_diffrn_reflns_theta_max         72.830
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             14256
_reflns_number_gt                11669
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    mercury
_computing_publication_material  ?
_refine_special_details          
;
One CH2Cl2 solvate molecule was found to be disordered and modeled over two sites. The relative sof's
were refined using a common Uiso for the Cl atoms and then the sof fixed.  To add H atoms the CH2Cl unit 
was modelled over two sites with common fractional atomic coordinates (EXYZ) and Uij (EADP) for the two 
components of C atom disorder and the two components of Cl atom disorder modelled anisotropically with
a common C-Cl bond distance (SADI). This reduced the residual electron density and improved the final R1 
and wR2 values.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1080P)²+2.8308P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14256
_refine_ls_number_parameters     1047
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1792
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl22 Cl 0.9076(2) 0.19265(18) 0.67994(14) 0.1249(8) Uani 1 1 d D . . . .
C20A C 0.9019(6) 0.0855(5) 0.7454(4) 0.105(2) Uani 0.5422 1 d D . P A 1
H20A H 0.851903 0.081204 0.793401 0.126 Uiso 0.5422 1 calc R U P A 1
H20B H 0.876116 0.043099 0.726281 0.126 Uiso 0.5422 1 calc R U P A 1
Cl21 Cl 1.0318(3) 0.0627(2) 0.7587(2) 0.1007(11) Uani 0.5422 1 d D . P A 1
C20B C 0.9019(6) 0.0855(5) 0.7454(4) 0.105(2) Uani 0.4578 1 d D . P A 2
H20C H 0.970261 0.059134 0.729557 0.126 Uiso 0.4578 1 calc R U P A 2
H20D H 0.843681 0.053008 0.738183 0.126 Uiso 0.4578 1 calc R U P A 2
Cl23 Cl 0.8820(5) 0.0585(3) 0.8448(3) 0.1138(15) Uani 0.4577 1 d D . P A 2
Br1 Br 1.13936(3) 0.12948(3) 0.52659(2) 0.04499(12) Uani 1 1 d . . . . .
Br8 Br 0.13097(7) 0.38394(4) 0.40618(3) 0.0867(2) Uani 1 1 d . . . . .
Cl1 Cl 0.52179(10) 0.40306(6) 0.09927(5) 0.0536(3) Uani 1 1 d . . . . .
Cl7 Cl -0.35867(7) 0.85414(7) 0.02307(6) 0.0519(2) Uani 1 1 d . . . . .
Cl6 Cl 0.63777(8) 0.97808(8) -0.19640(6) 0.0620(3) Uani 1 1 d . . . . .
Cl2 Cl 0.24868(11) -0.03669(12) 0.81619(7) 0.0838(5) Uani 1 1 d . . . . .
F105 F 0.46875(17) 0.59980(14) 0.06303(13) 0.0440(5) Uani 1 1 d . . . . .
F41 F 0.66463(16) 0.45137(13) 0.34707(12) 0.0409(5) Uani 1 1 d . . . . .
F42 F 0.80442(18) 0.55625(14) 0.22628(13) 0.0477(5) Uani 1 1 d . . . . .
O1 O 0.73357(16) 0.18268(13) 0.47325(12) 0.0281(4) Uani 1 1 d . . . . .
F51 F 0.82882(18) 0.29363(16) 0.52204(15) 0.0500(5) Uani 1 1 d . . . . .
O3 O 0.17388(17) 0.68320(14) 0.16499(12) 0.0306(4) Uani 1 1 d . . . . .
F95 F 0.28353(19) 0.50989(14) 0.17387(15) 0.0529(6) Uani 1 1 d . . . . .
F55 F 0.47567(18) 0.35164(18) 0.48437(14) 0.0519(6) Uani 1 1 d . . . . .
F43 F 0.99792(18) 0.49761(16) 0.17627(13) 0.0528(6) Uani 1 1 d . . . . .
F101 F 0.30656(19) 0.78790(17) 0.18933(15) 0.0526(6) Uani 1 1 d . . . . .
F104 F 0.63152(18) 0.58081(17) 0.13121(18) 0.0594(7) Uani 1 1 d . . . . .
F91 F 0.1815(2) 0.70903(18) -0.04195(14) 0.0561(6) Uani 1 1 d . . . . .
O4 O 0.14478(18) 0.89095(16) -0.01532(13) 0.0380(5) Uani 1 1 d . . . . .
F45 F 0.91293(19) 0.22464(15) 0.37000(14) 0.0540(6) Uani 1 1 d . . . . .
O2 O 0.4339(2) 0.16178(17) 0.45136(14) 0.0412(6) Uani 1 1 d . . . . .
F44 F 1.0522(2) 0.33254(19) 0.25235(17) 0.0664(8) Uani 1 1 d . . . . .
F54 F 0.4435(2) 0.43653(18) 0.57905(16) 0.0658(7) Uani 1 1 d . . . . .
F103 F 0.6360(2) 0.6679(2) 0.22753(18) 0.0715(8) Uani 1 1 d . . . . .
F102 F 0.4725(2) 0.7708(2) 0.25424(16) 0.0678(7) Uani 1 1 d . . . . .
N1 N 0.5925(2) 0.24556(17) 0.40843(14) 0.0277(5) Uani 1 1 d . . . . .
N6 N 0.2583(2) 0.78980(17) 0.04150(14) 0.0280(5) Uani 1 1 d . . . . .
N3 N 0.5586(2) 0.13197(17) 0.52520(14) 0.0277(5) Uani 1 1 d . . . . .
N7 N 0.0712(2) 0.77731(17) 0.09235(14) 0.0283(5) Uani 1 1 d . . . . .
F53 F 0.5995(3) 0.4511(2) 0.64896(16) 0.0763(9) Uani 1 1 d . . . . .
F52 F 0.7927(3) 0.3764(2) 0.62032(18) 0.0789(9) Uani 1 1 d . . . . .
F94 F 0.2404(2) 0.37619(16) 0.1348(2) 0.0829(11) Uani 1 1 d . . . . .
N2 N 0.7271(2) -0.09143(17) 0.64400(15) 0.0320(5) Uani 1 1 d . . . . .
N8 N -0.1468(3) 0.6905(2) 0.31450(17) 0.0432(7) Uani 1 1 d . . . . .
C3 C 0.0822(2) 0.71757(19) 0.15910(17) 0.0271(6) Uani 1 1 d . . . . .
C70 C -0.0336(2) 0.7976(2) 0.07650(16) 0.0279(6) Uani 1 1 d . . . . .
C10 C 0.5732(2) 0.2849(2) 0.33434(17) 0.0281(6) Uani 1 1 d . . . . .
C41 C 0.7593(2) 0.4184(2) 0.32449(18) 0.0299(6) Uani 1 1 d . . . . .
C40 C 0.7800(2) 0.3321(2) 0.36395(16) 0.0274(6) Uani 1 1 d . . . . .
C30 C 0.4791(2) 0.0895(2) 0.59375(17) 0.0291(6) Uani 1 1 d . . . . .
F92 F 0.1297(3) 0.5751(3) -0.0764(2) 0.0939(11) Uani 1 1 d . . . . .
C22 C 0.8288(3) -0.0495(2) 0.62332(17) 0.0306(6) Uani 1 1 d . . . . .
C2 C 0.6668(2) 0.12186(19) 0.52246(16) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.5210(2) 0.1819(2) 0.45797(17) 0.0287(6) Uani 1 1 d . . . . .
C80 C -0.0020(3) 0.6898(2) 0.22493(18) 0.0313(6) Uani 1 1 d . . . . .
C4 C 0.1628(2) 0.8257(2) 0.03329(17) 0.0286(6) Uani 1 1 d . . . . .
C42 C 0.8294(3) 0.4741(2) 0.26182(19) 0.0337(6) Uani 1 1 d . . . . .
F93 F 0.1592(3) 0.4069(3) 0.0099(3) 0.1046(14) Uani 1 1 d . . . . .
C50 C 0.6545(3) 0.31774(19) 0.49786(17) 0.0298(6) Uani 1 1 d . . . . .
C75 C -0.0924(3) 0.7327(2) 0.06938(18) 0.0319(6) Uani 1 1 d . . . . .
H75 H -0.063483 0.676506 0.075172 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6578(3) -0.0351(2) 0.61233(18) 0.0304(6) Uani 1 1 d . . . . .
C61 C 0.3801(3) 0.9212(2) -0.02470(19) 0.0326(6) Uani 1 1 d . . . . .
H61 H 0.339472 0.949545 0.006913 0.039 Uiso 1 1 calc R U . . .
C71 C -0.0743(3) 0.8806(2) 0.06823(19) 0.0325(6) Uani 1 1 d . . . . .
H71 H -0.033124 0.924867 0.073090 0.039 Uiso 1 1 calc R U . . .
C23 C 0.8221(2) 0.0381(2) 0.57521(16) 0.0275(6) Uani 1 1 d . . . . .
C83 C 0.0010(3) 0.6134(2) 0.29174(18) 0.0346(7) Uani 1 1 d . . . . .
C100 C 0.3753(3) 0.6896(2) 0.12657(18) 0.0308(6) Uani 1 1 d . . . . .
C24 C 0.9150(3) 0.0933(2) 0.54511(17) 0.0303(6) Uani 1 1 d . . . . .
H24 H 0.913799 0.152506 0.512253 0.036 Uiso 1 1 calc R U . . .
C26 C 1.0152(3) -0.0289(2) 0.6125(2) 0.0386(7) Uani 1 1 d . . . . .
H26 H 1.082234 -0.049969 0.623895 0.046 Uiso 1 1 calc R U . . .
C25 C 1.0091(3) 0.0578(2) 0.56535(19) 0.0343(7) Uani 1 1 d . . . . .
C90 C 0.2393(3) 0.6173(2) 0.0667(2) 0.0359(7) Uani 1 1 d . . . . .
C60 C 0.3511(2) 0.8357(2) -0.01452(17) 0.0295(6) Uani 1 1 d . . . . .
C43 C 0.9279(3) 0.4444(2) 0.23696(19) 0.0390(7) Uani 1 1 d . . . . .
C73 C -0.2335(3) 0.8323(2) 0.04528(19) 0.0352(7) Uani 1 1 d . . . . .
C27 C 0.9236(3) -0.0841(2) 0.64256(19) 0.0355(7) Uani 1 1 d . . . . .
H27 H 0.925621 -0.143380 0.675083 0.043 Uiso 1 1 calc R U . . .
C35 C 0.4857(3) 0.1108(2) 0.65574(19) 0.0360(7) Uani 1 1 d . . . . .
H35 H 0.539794 0.152248 0.651161 0.043 Uiso 1 1 calc R U . . .
C72 C -0.1758(3) 0.8976(2) 0.0528(2) 0.0348(7) Uani 1 1 d . . . . .
H72 H -0.205340 0.953498 0.047423 0.042 Uiso 1 1 calc R U . . .
C45 C 0.8811(3) 0.3065(2) 0.3367(2) 0.0354(7) Uani 1 1 d . . . . .
C101 C 0.3835(3) 0.7342(2) 0.1744(2) 0.0377(7) Uani 1 1 d . . . . .
C105 C 0.4632(3) 0.6409(2) 0.1124(2) 0.0350(7) Uani 1 1 d . . . . .
C11 C 0.6373(3) 0.2626(2) 0.2768(2) 0.0384(7) Uani 1 1 d . . . . .
H11 H 0.692562 0.222023 0.287229 0.046 Uiso 1 1 calc R U . . .
C81 C -0.0948(3) 0.7326(2) 0.2434(2) 0.0379(7) Uani 1 1 d . . . . .
C74 C -0.1933(3) 0.7497(2) 0.0538(2) 0.0374(7) Uani 1 1 d . . . . .
H74 H -0.234542 0.705341 0.049091 0.045 Uiso 1 1 calc R U . . .
C13 C 0.5423(3) 0.3576(2) 0.19007(18) 0.0361(7) Uani 1 1 d . . . . .
C15 C 0.4935(3) 0.3442(2) 0.31896(19) 0.0359(7) Uani 1 1 d . . . . .
H15 H 0.449468 0.359963 0.358148 0.043 Uiso 1 1 calc R U . . .
C31 C 0.3989(3) 0.0310(2) 0.5989(2) 0.0394(7) Uani 1 1 d . . . . .
H31 H 0.393545 0.017267 0.556417 0.047 Uiso 1 1 calc R U . . .
C65 C 0.4136(3) 0.7929(2) -0.0586(2) 0.0392(7) Uani 1 1 d . . . . .
H65 H 0.395335 0.733586 -0.050632 0.047 Uiso 1 1 calc R U . . .
C84 C 0.0695(3) 0.5440(2) 0.3093(2) 0.0407(8) Uani 1 1 d . . . . .
H84 H 0.132838 0.540206 0.274173 0.049 Uiso 1 1 calc R U . . .
C51 C 0.7306(3) 0.3269(2) 0.5358(2) 0.0379(7) Uani 1 1 d . . . . .
C82 C -0.0922(3) 0.6165(3) 0.34566(19) 0.0416(8) Uani 1 1 d . . . . .
C44 C 0.9547(3) 0.3610(3) 0.2749(2) 0.0423(8) Uani 1 1 d . . . . .
C55 C 0.5577(3) 0.3555(2) 0.5160(2) 0.0378(7) Uani 1 1 d . . . . .
C14 C 0.4773(3) 0.3808(2) 0.2467(2) 0.0395(7) Uani 1 1 d . . . . .
H14 H 0.422188 0.421344 0.236148 0.047 Uiso 1 1 calc R U . . .
C63 C 0.5269(3) 0.9228(3) -0.1253(2) 0.0398(8) Uani 1 1 d . . . . .
C12 C 0.6218(3) 0.2987(3) 0.2042(2) 0.0437(8) Uani 1 1 d . . . . .
H12 H 0.665556 0.282884 0.164890 0.052 Uiso 1 1 calc R U . . .
C64 C 0.5029(3) 0.8367(3) -0.1143(2) 0.0441(8) Uani 1 1 d . . . . .
H64 H 0.546374 0.807675 -0.144194 0.053 Uiso 1 1 calc R U . . .
C95 C 0.2502(3) 0.5292(2) 0.1095(2) 0.0429(8) Uani 1 1 d . . . . .
C104 C 0.5505(3) 0.6309(2) 0.1462(2) 0.0422(8) Uani 1 1 d . . . . .
C62 C 0.4680(3) 0.9657(2) -0.0806(2) 0.0394(7) Uani 1 1 d . . . . .
H62 H 0.487305 1.024608 -0.088110 0.047 Uiso 1 1 calc R U . . .
C102 C 0.4699(3) 0.7273(3) 0.2079(2) 0.0450(8) Uani 1 1 d . . . . .
C54 C 0.5380(3) 0.4000(3) 0.5659(2) 0.0461(9) Uani 1 1 d . . . . .
C34 C 0.4137(3) 0.0717(3) 0.7238(2) 0.0471(9) Uani 1 1 d . . . . .
H34 H 0.418556 0.085144 0.766542 0.057 Uiso 1 1 calc R U . . .
C28 C 0.7032(3) -0.1844(2) 0.6901(2) 0.0444(8) Uani 1 1 d . . . . .
H28A H 0.627690 -0.199622 0.694270 0.067 Uiso 1 1 calc R U . . .
H28B H 0.715250 -0.195235 0.740309 0.067 Uiso 1 1 calc R U . . .
H28C H 0.750516 -0.220661 0.666736 0.067 Uiso 1 1 calc R U . . .
C91 C 0.1986(3) 0.6279(3) 0.0046(2) 0.0452(8) Uani 1 1 d . . . . .
C103 C 0.5529(3) 0.6745(3) 0.1941(2) 0.0481(9) Uani 1 1 d . . . . .
C85 C 0.0407(4) 0.4811(3) 0.3802(2) 0.0525(10) Uani 1 1 d . . . . .
C52 C 0.7139(4) 0.3697(3) 0.5869(2) 0.0502(9) Uani 1 1 d . . . . .
C32 C 0.3263(3) -0.0071(3) 0.6676(2) 0.0518(10) Uani 1 1 d . . . . .
H32 H 0.270487 -0.047276 0.672455 0.062 Uiso 1 1 calc R U . . .
C87 C -0.1194(4) 0.5522(3) 0.4172(2) 0.0556(11) Uani 1 1 d . . . . .
H87 H -0.182208 0.555229 0.453117 0.067 Uiso 1 1 calc R U . . .
C53 C 0.6169(4) 0.4075(3) 0.6013(2) 0.0527(10) Uani 1 1 d . . . . .
C86 C -0.0499(4) 0.4831(3) 0.4335(2) 0.0603(12) Uani 1 1 d . . . . .
H86 H -0.064901 0.437345 0.481392 0.072 Uiso 1 1 calc R U . . .
B1 B 0.6885(3) 0.2713(2) 0.43410(19) 0.0261(6) Uani 1 1 d . . . . .
C33 C 0.3355(3) 0.0134(3) 0.7286(2) 0.0515(10) Uani 1 1 d . . . . .
B2 B 0.2652(3) 0.6955(2) 0.0959(2) 0.0306(7) Uani 1 1 d . . . . .
C94 C 0.2264(4) 0.4584(3) 0.0909(3) 0.0616(14) Uani 1 1 d . . . . .
C93 C 0.1854(4) 0.4747(4) 0.0278(3) 0.0680(15) Uani 1 1 d . . . . .
C92 C 0.1710(4) 0.5589(4) -0.0154(3) 0.0628(13) Uani 1 1 d . . . . .
C88 C -0.2429(4) 0.7214(4) 0.3543(3) 0.0653(13) Uani 1 1 d . . . . .
H88A H -0.298852 0.673810 0.377907 0.098 Uiso 1 1 calc R U . . .
H88B H -0.270182 0.771862 0.318525 0.098 Uiso 1 1 calc R U . . .
H88C H -0.223897 0.739261 0.393006 0.098 Uiso 1 1 calc R U . . .
C20 C 0.7101(2) 0.0465(2) 0.56946(17) 0.0280(6) Uani 1 1 d . . . . .
C300 C -0.0069(5) 0.8163(6) -0.1323(4) 0.093(2) Uani 1 1 d . . . . .
H30A H -0.010691 0.763426 -0.086464 0.112 Uiso 1 1 calc R U . . .
H30B H 0.020219 0.866673 -0.123073 0.112 Uiso 1 1 calc R U . . .
Cl31 Cl 0.08443(14) 0.79959(14) -0.20670(10) 0.0914(5) Uani 1 1 d . . . . .
Cl32 Cl -0.13477(13) 0.83665(14) -0.14769(9) 0.0926(5) Uani 1 1 d . . . . .
H81 H -0.126(4) 0.786(3) 0.215(3) 0.047(12) Uiso 1 1 d . . . . .
H21 H 0.588(3) -0.058(2) 0.624(2) 0.023(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl22 C20B 1.749(8) . ?
Cl22 C20A 1.749(8) . ?
C20A Cl21 1.736(8) . ?
C20B Cl23 1.793(8) . ?
Br1 C25 1.907(3) . ?
Br8 C85 1.903(5) . ?
Cl1 C13 1.740(3) . ?
Cl7 C73 1.734(3) . ?
Cl6 C63 1.750(3) . ?
Cl2 C33 1.746(4) . ?
F105 C105 1.345(4) . ?
F41 C41 1.346(4) . ?
F42 C42 1.331(4) . ?
O1 C2 1.284(4) . ?
O1 B1 1.529(4) . ?
F51 C51 1.352(4) . ?
O3 C3 1.285(4) . ?
O3 B2 1.528(4) . ?
F95 C95 1.346(5) . ?
F55 C55 1.342(5) . ?
F43 C43 1.344(4) . ?
F101 C101 1.339(4) . ?
F104 C104 1.333(4) . ?
F91 C91 1.352(5) . ?
O4 C4 1.201(4) . ?
F45 C45 1.348(4) . ?
O2 C1 1.215(4) . ?
F44 C44 1.342(4) . ?
F54 C54 1.333(5) . ?
F103 C103 1.346(4) . ?
F102 C102 1.340(5) . ?
N1 C1 1.342(4) . ?
N1 C10 1.434(4) . ?
N1 B1 1.545(4) . ?
N6 C4 1.345(4) . ?
N6 C60 1.435(4) . ?
N6 B2 1.537(4) . ?
N3 C2 1.372(4) . ?
N3 C30 1.444(4) . ?
N3 C1 1.452(4) . ?
N7 C3 1.355(4) . ?
N7 C70 1.436(4) . ?
N7 C4 1.460(4) . ?
F53 C53 1.337(4) . ?
F52 C52 1.340(5) . ?
F94 C94 1.337(6) . ?
N2 C21 1.333(4) . ?
N2 C22 1.393(4) . ?
N2 C28 1.461(4) . ?
N8 C81 1.336(5) . ?
N8 C82 1.380(5) . ?
N8 C88 1.469(5) . ?
C3 C80 1.419(4) . ?
C70 C75 1.381(5) . ?
C70 C71 1.394(4) . ?
C10 C15 1.379(4) . ?
C10 C11 1.385(5) . ?
C41 C42 1.379(5) . ?
C41 C40 1.388(4) . ?
C40 C45 1.387(4) . ?
C40 B1 1.619(4) . ?
C30 C31 1.385(5) . ?
C30 C35 1.395(5) . ?
F92 C92 1.347(6) . ?
C22 C27 1.384(5) . ?
C22 C23 1.412(4) . ?
C2 C20 1.423(4) . ?
C80 C81 1.390(5) . ?
C80 C83 1.454(4) . ?
C42 C43 1.374(5) . ?
F93 C93 1.344(5) . ?
C50 C51 1.386(5) . ?
C50 C55 1.386(5) . ?
C50 B1 1.647(4) . ?
C75 C74 1.380(5) . ?
C21 C20 1.390(4) . ?
C61 C62 1.385(5) . ?
C61 C60 1.385(5) . ?
C71 C72 1.387(5) . ?
C23 C24 1.394(5) . ?
C23 C20 1.453(4) . ?
C83 C84 1.390(5) . ?
C83 C82 1.412(5) . ?
C100 C105 1.380(5) . ?
C100 C101 1.394(5) . ?
C100 B2 1.630(5) . ?
C24 C25 1.386(5) . ?
C26 C27 1.383(5) . ?
C26 C25 1.393(5) . ?
C90 C91 1.378(6) . ?
C90 C95 1.398(5) . ?
C90 B2 1.640(5) . ?
C60 C65 1.391(5) . ?
C43 C44 1.367(5) . ?
C73 C72 1.382(5) . ?
C73 C74 1.385(5) . ?
C35 C34 1.382(5) . ?
C45 C44 1.385(5) . ?
C101 C102 1.384(5) . ?
C105 C104 1.392(5) . ?
C11 C12 1.388(5) . ?
C13 C12 1.371(5) . ?
C13 C14 1.383(5) . ?
C15 C14 1.384(5) . ?
C31 C32 1.392(6) . ?
C65 C64 1.393(5) . ?
C84 C85 1.376(5) . ?
C51 C52 1.386(5) . ?
C82 C87 1.394(5) . ?
C55 C54 1.384(5) . ?
C63 C64 1.375(6) . ?
C63 C62 1.381(5) . ?
C95 C94 1.387(6) . ?
C104 C103 1.366(6) . ?
C102 C103 1.375(6) . ?
C54 C53 1.372(7) . ?
C34 C33 1.367(6) . ?
C91 C92 1.393(6) . ?
C85 C86 1.378(7) . ?
C52 C53 1.374(7) . ?
C32 C33 1.377(7) . ?
C87 C86 1.392(8) . ?
C94 C93 1.382(9) . ?
C93 C92 1.360(8) . ?
C300 Cl32 1.719(7) . ?
C300 Cl31 1.743(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl21 C20A Cl22 107.0(4) . . ?
Cl22 C20B Cl23 124.6(5) . . ?
C2 O1 B1 117.8(2) . . ?
C3 O3 B2 121.5(2) . . ?
C1 N1 C10 116.5(3) . . ?
C1 N1 B1 118.8(2) . . ?
C10 N1 B1 124.7(2) . . ?
C4 N6 C60 116.0(2) . . ?
C4 N6 B2 121.6(3) . . ?
C60 N6 B2 121.0(2) . . ?
C2 N3 C30 121.0(2) . . ?
C2 N3 C1 120.6(3) . . ?
C30 N3 C1 118.3(2) . . ?
C3 N7 C70 120.9(3) . . ?
C3 N7 C4 123.0(3) . . ?
C70 N7 C4 116.1(2) . . ?
C21 N2 C22 109.7(3) . . ?
C21 N2 C28 125.9(3) . . ?
C22 N2 C28 124.4(3) . . ?
C81 N8 C82 109.2(3) . . ?
C81 N8 C88 125.1(4) . . ?
C82 N8 C88 125.6(3) . . ?
O3 C3 N7 119.4(3) . . ?
O3 C3 C80 116.4(3) . . ?
N7 C3 C80 124.1(3) . . ?
C75 C70 C71 121.1(3) . . ?
C75 C70 N7 118.1(3) . . ?
C71 C70 N7 120.8(3) . . ?
C15 C10 C11 119.5(3) . . ?
C15 C10 N1 122.0(3) . . ?
C11 C10 N1 118.5(3) . . ?
F41 C41 C42 116.4(3) . . ?
F41 C41 C40 119.3(3) . . ?
C42 C41 C40 124.3(3) . . ?
C45 C40 C41 113.9(3) . . ?
C45 C40 B1 126.3(3) . . ?
C41 C40 B1 119.7(3) . . ?
C31 C30 C35 120.7(3) . . ?
C31 C30 N3 122.7(3) . . ?
C35 C30 N3 116.6(3) . . ?
C27 C22 N2 128.5(3) . . ?
C27 C22 C23 123.3(3) . . ?
N2 C22 C23 108.2(3) . . ?
O1 C2 N3 118.4(3) . . ?
O1 C2 C20 117.7(3) . . ?
N3 C2 C20 123.9(3) . . ?
O2 C1 N1 127.8(3) . . ?
O2 C1 N3 119.2(3) . . ?
N1 C1 N3 113.0(3) . . ?
C81 C80 C3 129.0(3) . . ?
C81 C80 C83 106.0(3) . . ?
C3 C80 C83 124.6(3) . . ?
O4 C4 N6 128.5(3) . . ?
O4 C4 N7 117.7(3) . . ?
N6 C4 N7 113.9(3) . . ?
F42 C42 C43 119.7(3) . . ?
F42 C42 C41 121.4(3) . . ?
C43 C42 C41 118.9(3) . . ?
C51 C50 C55 113.6(3) . . ?
C51 C50 B1 119.1(3) . . ?
C55 C50 B1 127.2(3) . . ?
C74 C75 C70 119.9(3) . . ?
N2 C21 C20 110.0(3) . . ?
C62 C61 C60 120.5(3) . . ?
C72 C71 C70 119.0(3) . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 C20 135.6(3) . . ?
C22 C23 C20 105.3(3) . . ?
C84 C83 C82 119.9(3) . . ?
C84 C83 C80 134.7(3) . . ?
C82 C83 C80 105.4(3) . . ?
C105 C100 C101 114.4(3) . . ?
C105 C100 B2 126.4(3) . . ?
C101 C100 B2 119.2(3) . . ?
C25 C24 C23 116.9(3) . . ?
C27 C26 C25 119.8(3) . . ?
C24 C25 C26 123.6(3) . . ?
C24 C25 Br1 119.3(3) . . ?
C26 C25 Br1 117.0(2) . . ?
C91 C90 C95 113.6(3) . . ?
C91 C90 B2 126.4(3) . . ?
C95 C90 B2 119.9(3) . . ?
C61 C60 C65 119.7(3) . . ?
C61 C60 N6 121.2(3) . . ?
C65 C60 N6 119.1(3) . . ?
F43 C43 C44 120.3(3) . . ?
F43 C43 C42 120.1(3) . . ?
C44 C43 C42 119.6(3) . . ?
C72 C73 C74 121.7(3) . . ?
C72 C73 Cl7 119.6(3) . . ?
C74 C73 Cl7 118.7(3) . . ?
C26 C27 C22 117.2(3) . . ?
C34 C35 C30 120.1(3) . . ?
C73 C72 C71 119.3(3) . . ?
F45 C45 C44 116.0(3) . . ?
F45 C45 C40 120.5(3) . . ?
C44 C45 C40 123.5(3) . . ?
F101 C101 C102 116.3(3) . . ?
F101 C101 C100 120.5(3) . . ?
C102 C101 C100 123.2(3) . . ?
F105 C105 C100 120.2(3) . . ?
F105 C105 C104 115.7(3) . . ?
C100 C105 C104 124.0(3) . . ?
C10 C11 C12 120.8(3) . . ?
N8 C81 C80 110.7(3) . . ?
C75 C74 C73 119.0(3) . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 Cl1 119.2(3) . . ?
C14 C13 Cl1 119.5(3) . . ?
C10 C15 C14 120.3(3) . . ?
C30 C31 C32 118.5(4) . . ?
C60 C65 C64 120.1(3) . . ?
C85 C84 C83 116.5(4) . . ?
F51 C51 C52 116.5(3) . . ?
F51 C51 C50 119.1(3) . . ?
C52 C51 C50 124.4(4) . . ?
N8 C82 C87 128.7(4) . . ?
N8 C82 C83 108.7(3) . . ?
C87 C82 C83 122.6(4) . . ?
F44 C44 C43 119.9(3) . . ?
F44 C44 C45 120.4(3) . . ?
C43 C44 C45 119.7(3) . . ?
F55 C55 C54 115.3(3) . . ?
F55 C55 C50 120.7(3) . . ?
C54 C55 C50 124.0(4) . . ?
C13 C14 C15 119.3(3) . . ?
C64 C63 C62 121.9(3) . . ?
C64 C63 Cl6 118.6(3) . . ?
C62 C63 Cl6 119.5(3) . . ?
C13 C12 C11 118.8(3) . . ?
C63 C64 C65 118.8(3) . . ?
F95 C95 C94 116.6(4) . . ?
F95 C95 C90 119.2(3) . . ?
C94 C95 C90 124.1(4) . . ?
F104 C104 C103 120.5(3) . . ?
F104 C104 C105 120.7(4) . . ?
C103 C104 C105 118.8(3) . . ?
C63 C62 C61 118.8(3) . . ?
F102 C102 C103 120.0(4) . . ?
F102 C102 C101 120.5(4) . . ?
C103 C102 C101 119.5(4) . . ?
F54 C54 C53 119.8(4) . . ?
F54 C54 C55 120.4(4) . . ?
C53 C54 C55 119.7(4) . . ?
C33 C34 C35 118.7(4) . . ?
F91 C91 C90 120.9(3) . . ?
F91 C91 C92 114.6(4) . . ?
C90 C91 C92 124.5(4) . . ?
F103 C103 C104 121.2(4) . . ?
F103 C103 C102 118.8(4) . . ?
C104 C103 C102 119.9(3) . . ?
C84 C85 C86 124.4(4) . . ?
C84 C85 Br8 118.0(4) . . ?
C86 C85 Br8 117.6(3) . . ?
F52 C52 C53 120.5(4) . . ?
F52 C52 C51 120.3(4) . . ?
C53 C52 C51 119.2(4) . . ?
C33 C32 C31 119.9(4) . . ?
C86 C87 C82 116.5(4) . . ?
F53 C53 C54 120.4(4) . . ?
F53 C53 C52 120.5(4) . . ?
C54 C53 C52 119.1(3) . . ?
C85 C86 C87 120.1(4) . . ?
O1 B1 N1 103.5(2) . . ?
O1 B1 C40 110.2(2) . . ?
N1 B1 C40 112.1(2) . . ?
O1 B1 C50 105.8(2) . . ?
N1 B1 C50 114.6(2) . . ?
C40 B1 C50 110.2(2) . . ?
C34 C33 C32 122.0(4) . . ?
C34 C33 Cl2 117.3(3) . . ?
C32 C33 Cl2 120.7(3) . . ?
O3 B2 N6 106.0(2) . . ?
O3 B2 C100 104.5(3) . . ?
N6 B2 C100 108.7(3) . . ?
O3 B2 C90 103.8(3) . . ?
N6 B2 C90 115.1(3) . . ?
C100 B2 C90 117.4(3) . . ?
F94 C94 C93 121.3(4) . . ?
F94 C94 C95 120.0(5) . . ?
C93 C94 C95 118.7(4) . . ?
F93 C93 C92 120.3(6) . . ?
F93 C93 C94 119.6(5) . . ?
C92 C93 C94 120.1(4) . . ?
F92 C92 C93 120.3(4) . . ?
F92 C92 C91 120.6(5) . . ?
C93 C92 C91 119.1(5) . . ?
C21 C20 C2 127.4(3) . . ?
C21 C20 C23 106.9(3) . . ?
C2 C20 C23 125.5(3) . . ?
Cl32 C300 Cl31 113.6(4) . . ?

_refine_diff_density_max         1.385
_refine_diff_density_min         -1.455
_refine_diff_density_rms         0.095

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rm2211_a
_database_code_depnum_ccdc_archive 'CCDC 2163272'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2022-03-30 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 Cl N2 O Si'
_chemical_formula_sum            'C25 H25 Cl N2 O Si'
_chemical_formula_weight         433.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0506(6)
_cell_length_b                   12.4111(9)
_cell_length_c                   19.1784(12)
_cell_angle_alpha                99.504(5)
_cell_angle_beta                 93.559(5)
_cell_angle_gamma                90.568(5)
_cell_volume                     2354.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3792
_cell_measurement_theta_min      3.9170
_cell_measurement_theta_max      71.9810

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    2.060
_shelx_estimated_absorpt_T_min   0.714
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17234
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.611
_diffrn_reflns_theta_max         72.796
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9111
_reflns_number_gt                5796
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP, SHELXL, Mercury'
_computing_publication_material  publCIF
_refine_special_details          
;
The TMS group on Si2 was disordered and refined over two sites
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9111
_refine_ls_number_parameters     578
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1677
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41165(19) 0.66816(18) 0.79836(12) 0.0424(5) Uani 1 1 d . . . . .
N1 N 0.2703(2) 0.60871(19) 0.87207(12) 0.0336(5) Uani 1 1 d . . . . .
C1 C 0.2964(3) 0.6576(2) 0.81529(15) 0.0320(5) Uani 1 1 d . . . . .
N2 N 0.1884(2) 0.69488(19) 0.78043(13) 0.0349(5) Uani 1 1 d . . . . .
H2 H 0.110877 0.690449 0.798789 0.042 Uiso 1 1 calc R U . . .
C2 C 0.7955(3) 0.7483(2) 0.81837(14) 0.0317(5) Uani 1 1 d . . . . .
N3 N 0.6896(2) 0.6930(2) 0.78152(13) 0.0362(5) Uani 1 1 d . . . . .
H3 H 0.611138 0.699892 0.799534 0.043 Uiso 1 1 calc R U . . .
O2 O 0.91190(18) 0.73030(17) 0.80433(11) 0.0394(5) Uani 1 1 d . . . . .
N4 N 0.7675(2) 0.82583(19) 0.87547(12) 0.0326(5) Uani 1 1 d . . . . .
C10 C 0.3837(3) 0.5736(2) 0.91504(17) 0.0402(6) Uani 1 1 d . . . . .
H00D H 0.357509 0.576147 0.964195 0.048 Uiso 1 1 calc R U . . .
H00E H 0.459160 0.625898 0.916402 0.048 Uiso 1 1 calc R U . . .
C16 C 0.3633(3) 0.3682(3) 0.90207(17) 0.0457(7) Uani 1 1 d . . . . .
H16 H 0.288111 0.377341 0.930021 0.055 Uiso 1 1 calc R U . . .
Cl1 Cl 0.15828(14) 0.90301(11) 0.52393(6) 0.0858(4) Uani 1 1 d . . . . .
Si1 Si 0.22050(11) 0.32267(10) 0.65162(6) 0.0610(3) Uani 1 1 d . . . . .
C11 C 0.4301(3) 0.4597(2) 0.88745(16) 0.0369(6) Uani 1 1 d . . . . .
C12 C 0.5398(3) 0.4436(3) 0.8474(2) 0.0508(8) Uani 1 1 d . . . . .
H12 H 0.587256 0.505081 0.837061 0.061 Uiso 1 1 calc R U . . .
C13 C 0.5818(4) 0.3398(3) 0.8222(2) 0.0601(9) Uani 1 1 d . . . . .
H13 H 0.657289 0.330445 0.794530 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5150(4) 0.2498(3) 0.8368(2) 0.0562(9) Uani 1 1 d . . . . .
H14 H 0.544475 0.178375 0.819780 0.067 Uiso 1 1 calc R U . . .
C15 C 0.4049(4) 0.2642(3) 0.87643(19) 0.0532(8) Uani 1 1 d . . . . .
H15 H 0.357346 0.202429 0.886156 0.064 Uiso 1 1 calc R U . . .
C20 C 0.1901(3) 0.7399(2) 0.71763(14) 0.0340(6) Uani 1 1 d . . . . .
C21 C 0.2927(3) 0.8080(3) 0.70408(17) 0.0434(7) Uani 1 1 d . . . . .
H21 H 0.369254 0.821400 0.736148 0.052 Uiso 1 1 calc R U . . .
C22 C 0.2834(4) 0.8563(3) 0.64405(19) 0.0526(8) Uani 1 1 d . . . . .
H22 H 0.353734 0.902457 0.634610 0.063 Uiso 1 1 calc R U . . .
C23 C 0.1729(4) 0.8374(3) 0.59832(17) 0.0543(8) Uani 1 1 d . . . . .
C24 C 0.0714(4) 0.7684(4) 0.60972(19) 0.0636(10) Uani 1 1 d . . . . .
H24 H -0.004063 0.754551 0.576926 0.076 Uiso 1 1 calc R U . . .
C25 C 0.0807(3) 0.7197(3) 0.66939(17) 0.0504(8) Uani 1 1 d . . . . .
H25 H 0.011251 0.671695 0.677528 0.061 Uiso 1 1 calc R U . . .
C30 C 0.1387(3) 0.5862(2) 0.89052(15) 0.0337(6) Uani 1 1 d . . . . .
C31 C 0.0901(3) 0.6471(2) 0.95062(16) 0.0391(6) Uani 1 1 d . . . . .
H31 H 0.144503 0.702995 0.978640 0.047 Uiso 1 1 calc R U . . .
C32 C -0.0380(3) 0.6268(3) 0.97021(17) 0.0449(7) Uani 1 1 d . . . . .
H32 H -0.070875 0.668986 1.011251 0.054 Uiso 1 1 calc R U . . .
C33 C -0.1162(3) 0.5458(3) 0.93010(18) 0.0474(7) Uani 1 1 d . . . . .
H33 H -0.203663 0.532255 0.943179 0.057 Uiso 1 1 calc R U . . .
C34 C -0.0682(3) 0.4834(3) 0.87036(17) 0.0439(7) Uani 1 1 d . . . . .
H34 H -0.122975 0.426632 0.843467 0.053 Uiso 1 1 calc R U . . .
C35 C 0.0592(3) 0.5027(2) 0.84907(15) 0.0357(6) Uani 1 1 d . . . . .
C36 C 0.1064(3) 0.4406(2) 0.78432(18) 0.0434(7) Uani 1 1 d . . . . .
C37 C 0.1435(3) 0.3955(3) 0.73384(19) 0.0462(7) Uani 1 1 d . . . . .
C38 C 0.3850(5) 0.3877(5) 0.6472(3) 0.0889(15) Uani 1 1 d . . . . .
H01E H 0.425999 0.353495 0.604207 0.133 Uiso 1 1 calc R U . . .
H38 H 0.442432 0.378299 0.688903 0.133 Uiso 1 1 calc R U . . .
H01K H 0.373972 0.465792 0.646221 0.133 Uiso 1 1 calc R U . . .
C39 C 0.1148(6) 0.3346(8) 0.5726(3) 0.133(3) Uani 1 1 d . . . . .
H01O H 0.160458 0.304087 0.530311 0.199 Uiso 1 1 calc R U . . .
H01P H 0.096457 0.411789 0.571718 0.199 Uiso 1 1 calc R U . . .
H01Q H 0.030640 0.294356 0.573330 0.199 Uiso 1 1 calc R U . . .
Cl2 Cl 0.71885(14) 0.40221(14) 0.50509(6) 0.1015(5) Uani 1 1 d . . . . .
C40 C 0.2391(7) 0.1762(4) 0.6619(4) 0.113(2) Uani 1 1 d . . . . .
H01L H 0.150707 0.142351 0.662349 0.169 Uiso 1 1 calc R U . . .
H01M H 0.290280 0.172030 0.706549 0.169 Uiso 1 1 calc R U . . .
H01N H 0.286040 0.137496 0.622258 0.169 Uiso 1 1 calc R U . . .
C50 C 0.6997(3) 0.6242(2) 0.71487(15) 0.0354(6) Uani 1 1 d . . . . .
C51 C 0.6128(3) 0.6369(3) 0.65904(19) 0.0536(8) Uani 1 1 d . . . . .
H51 H 0.548057 0.692417 0.664923 0.064 Uiso 1 1 calc R U . . .
C52 C 0.6184(4) 0.5692(4) 0.5937(2) 0.0657(10) Uani 1 1 d . . . . .
H52 H 0.558369 0.578391 0.554990 0.079 Uiso 1 1 calc R U . . .
C53 C 0.7119(4) 0.4890(3) 0.58623(19) 0.0585(9) Uani 1 1 d . . . . .
C54 C 0.7980(4) 0.4744(3) 0.6414(2) 0.0553(9) Uani 1 1 d . . . . .
H54 H 0.861267 0.417783 0.635586 0.066 Uiso 1 1 calc R U . . .
C55 C 0.7928(3) 0.5421(3) 0.70592(17) 0.0450(7) Uani 1 1 d . . . . .
H55 H 0.853288 0.532451 0.744365 0.054 Uiso 1 1 calc R U . . .
C60 C 0.8801(3) 0.8838(2) 0.91899(15) 0.0375(6) Uani 1 1 d . . . . .
H00B H 0.954747 0.832735 0.921192 0.045 Uiso 1 1 calc R U . . .
H00C H 0.852677 0.906675 0.967829 0.045 Uiso 1 1 calc R U . . .
C61 C 0.9290(3) 0.9832(2) 0.89140(16) 0.0359(6) Uani 1 1 d . . . . .
C62 C 0.8649(3) 1.0825(3) 0.90540(18) 0.0463(7) Uani 1 1 d . . . . .
H62 H 0.789986 1.088051 0.933549 0.056 Uiso 1 1 calc R U . . .
C63 C 0.9079(4) 1.1730(3) 0.8793(2) 0.0539(8) Uani 1 1 d . . . . .
H63 H 0.861393 1.239684 0.888268 0.065 Uiso 1 1 calc R U . . .
C64 C 1.0190(4) 1.1660(3) 0.8399(2) 0.0557(9) Uani 1 1 d . . . . .
H64 H 1.050831 1.228466 0.822777 0.067 Uiso 1 1 calc R U . . .
C65 C 1.0835(3) 1.0679(3) 0.8255(2) 0.0578(9) Uani 1 1 d . . . . .
H65 H 1.159057 1.062839 0.797803 0.069 Uiso 1 1 calc R U . . .
C66 C 1.0393(3) 0.9775(3) 0.85093(19) 0.0464(7) Uani 1 1 d . . . . .
H66 H 1.084726 0.910569 0.840701 0.056 Uiso 1 1 calc R U . . .
C70 C 0.6349(3) 0.8570(2) 0.89176(14) 0.0317(5) Uani 1 1 d . . . . .
C71 C 0.5846(3) 0.8277(2) 0.95212(15) 0.0366(6) Uani 1 1 d . . . . .
H71 H 0.637977 0.787228 0.980833 0.044 Uiso 1 1 calc R U . . .
C72 C 0.4571(3) 0.8570(3) 0.97068(17) 0.0429(7) Uani 1 1 d . . . . .
H72 H 0.423500 0.836809 1.012003 0.052 Uiso 1 1 calc R U . . .
C73 C 0.3791(3) 0.9157(3) 0.92899(17) 0.0443(7) Uani 1 1 d . . . . .
H73 H 0.291578 0.935290 0.941536 0.053 Uiso 1 1 calc R U . . .
C74 C 0.4281(3) 0.9461(2) 0.86894(17) 0.0415(6) Uani 1 1 d . . . . .
H74 H 0.373915 0.986699 0.840760 0.050 Uiso 1 1 calc R U . . .
C75 C 0.5573(3) 0.9174(2) 0.84926(15) 0.0338(6) Uani 1 1 d . . . . .
C76 C 0.6055(3) 0.9468(2) 0.78494(17) 0.0406(6) Uani 1 1 d . . . . .
C77 C 0.6389(3) 0.9691(3) 0.73231(18) 0.0473(7) Uani 1 1 d . . . . .
Si2 Si 0.69908(10) 1.00648(9) 0.64875(5) 0.0525(2) Uani 1 1 d D . . . .
C78A C 0.5837(15) 0.9684(19) 0.5730(7) 0.109(10) Uani 0.2648 1 d D . P A 1
H78A H 0.610938 1.003674 0.533914 0.164 Uiso 0.2648 1 calc R U P A 1
H78B H 0.494054 0.991867 0.585308 0.164 Uiso 0.2648 1 calc R U P A 1
H78C H 0.583048 0.888876 0.558494 0.164 Uiso 0.2648 1 calc R U P A 1
C79A C 0.8609(15) 0.9392(18) 0.6403(11) 0.110(9) Uani 0.2648 1 d D . P A 1
H79A H 0.910029 0.968191 0.604615 0.165 Uiso 0.2648 1 calc R U P A 1
H79B H 0.846265 0.860262 0.625641 0.165 Uiso 0.2648 1 calc R U P A 1
H79C H 0.912606 0.953161 0.685970 0.165 Uiso 0.2648 1 calc R U P A 1
C80A C 0.729(2) 1.1600(9) 0.6668(10) 0.097(7) Uani 0.2648 1 d D . P A 1
H80A H 0.744800 1.185708 0.622293 0.145 Uiso 0.2648 1 calc R U P A 1
H80B H 0.807664 1.177597 0.699945 0.145 Uiso 0.2648 1 calc R U P A 1
H80C H 0.651155 1.195846 0.687479 0.145 Uiso 0.2648 1 calc R U P A 1
C78B C 0.6731(8) 0.8824(6) 0.5770(3) 0.090(2) Uani 0.7352 1 d D . P A 2
H78D H 0.705397 0.898974 0.532651 0.135 Uiso 0.7352 1 calc R U P A 2
H78E H 0.577906 0.862961 0.569941 0.135 Uiso 0.7352 1 calc R U P A 2
H78F H 0.722548 0.820996 0.591113 0.135 Uiso 0.7352 1 calc R U P A 2
C79B C 0.8762(6) 1.0407(8) 0.6630(4) 0.092(2) Uani 0.7352 1 d D . P A 2
H79D H 0.912329 1.048848 0.617809 0.138 Uiso 0.7352 1 calc R U P A 2
H79E H 0.922731 0.982257 0.682568 0.138 Uiso 0.7352 1 calc R U P A 2
H79F H 0.889023 1.109464 0.696317 0.138 Uiso 0.7352 1 calc R U P A 2
C80B C 0.5976(8) 1.1175(7) 0.6248(4) 0.110(3) Uani 0.7352 1 d D . P A 2
H80D H 0.600908 1.118726 0.573972 0.166 Uiso 0.7352 1 calc R U P A 2
H80E H 0.632305 1.187285 0.651659 0.166 Uiso 0.7352 1 calc R U P A 2
H80F H 0.505168 1.106280 0.635924 0.166 Uiso 0.7352 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.233(3) . ?
N1 C1 1.369(4) . ?
N1 C30 1.426(4) . ?
N1 C10 1.477(4) . ?
C1 N2 1.364(4) . ?
N2 C20 1.410(4) . ?
N2 H2 0.8800 . ?
C2 O2 1.231(3) . ?
C2 N3 1.355(4) . ?
C2 N4 1.379(4) . ?
N3 C50 1.425(4) . ?
N3 H3 0.8800 . ?
N4 C70 1.430(3) . ?
N4 C60 1.471(4) . ?
C10 C11 1.514(4) . ?
C10 H00D 0.9900 . ?
C10 H00E 0.9900 . ?
C16 C15 1.382(5) . ?
C16 C11 1.389(4) . ?
C16 H16 0.9500 . ?
Cl1 C23 1.755(3) . ?
Si1 C39 1.823(6) . ?
Si1 C38 1.845(5) . ?
Si1 C40 1.871(6) . ?
Si1 C37 1.896(3) . ?
C11 C12 1.380(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C20 C25 1.385(4) . ?
C20 C21 1.391(4) . ?
C21 C22 1.382(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.365(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(6) . ?
C24 C25 1.378(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C30 C31 1.388(4) . ?
C30 C35 1.407(4) . ?
C31 C32 1.396(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.368(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.398(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.458(5) . ?
C36 C37 1.123(5) . ?
C38 H01E 0.9800 . ?
C38 H38 0.9800 . ?
C38 H01K 0.9800 . ?
C39 H01O 0.9800 . ?
C39 H01P 0.9800 . ?
C39 H01Q 0.9800 . ?
Cl2 C53 1.746(3) . ?
C40 H01L 0.9800 . ?
C40 H01M 0.9800 . ?
C40 H01N 0.9800 . ?
C50 C51 1.370(5) . ?
C50 C55 1.388(4) . ?
C51 C52 1.393(5) . ?
C51 H51 0.9500 . ?
C52 C53 1.372(6) . ?
C52 H52 0.9500 . ?
C53 C54 1.362(5) . ?
C54 C55 1.380(5) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C60 C61 1.510(4) . ?
C60 H00B 0.9900 . ?
C60 H00C 0.9900 . ?
C61 C62 1.390(4) . ?
C61 C66 1.388(4) . ?
C62 C63 1.380(5) . ?
C62 H62 0.9500 . ?
C63 C64 1.382(5) . ?
C63 H63 0.9500 . ?
C64 C65 1.380(5) . ?
C64 H64 0.9500 . ?
C65 C66 1.375(5) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C70 C71 1.392(4) . ?
C70 C75 1.403(4) . ?
C71 C72 1.387(4) . ?
C71 H71 0.9500 . ?
C72 C73 1.382(5) . ?
C72 H72 0.9500 . ?
C73 C74 1.386(5) . ?
C73 H73 0.9500 . ?
C74 C75 1.407(4) . ?
C74 H74 0.9500 . ?
C75 C76 1.452(4) . ?
C76 C77 1.158(5) . ?
C77 Si2 1.873(3) . ?
Si2 C78A 1.798(11) . ?
Si2 C79B 1.820(6) . ?
Si2 C80B 1.825(6) . ?
Si2 C79A 1.840(11) . ?
Si2 C80A 1.897(12) . ?
Si2 C78B 1.893(6) . ?
C78A H78A 0.9800 . ?
C78A H78B 0.9800 . ?
C78A H78C 0.9800 . ?
C79A H79A 0.9800 . ?
C79A H79B 0.9800 . ?
C79A H79C 0.9800 . ?
C80A H80A 0.9800 . ?
C80A H80B 0.9800 . ?
C80A H80C 0.9800 . ?
C78B H78D 0.9800 . ?
C78B H78E 0.9800 . ?
C78B H78F 0.9800 . ?
C79B H79D 0.9800 . ?
C79B H79E 0.9800 . ?
C79B H79F 0.9800 . ?
C80B H80D 0.9800 . ?
C80B H80E 0.9800 . ?
C80B H80F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C30 123.4(2) . . ?
C1 N1 C10 118.5(2) . . ?
C30 N1 C10 118.0(2) . . ?
O1 C1 N2 123.0(3) . . ?
O1 C1 N1 121.0(3) . . ?
N2 C1 N1 115.9(2) . . ?
C1 N2 C20 125.8(2) . . ?
C1 N2 H2 117.1 . . ?
C20 N2 H2 117.1 . . ?
O2 C2 N3 123.5(2) . . ?
O2 C2 N4 120.1(3) . . ?
N3 C2 N4 116.4(2) . . ?
C2 N3 C50 122.9(2) . . ?
C2 N3 H3 118.5 . . ?
C50 N3 H3 118.5 . . ?
C2 N4 C70 123.2(2) . . ?
C2 N4 C60 118.1(2) . . ?
C70 N4 C60 118.6(2) . . ?
N1 C10 C11 113.7(2) . . ?
N1 C10 H00D 108.8 . . ?
C11 C10 H00D 108.8 . . ?
N1 C10 H00E 108.8 . . ?
C11 C10 H00E 108.8 . . ?
H00D C10 H00E 107.7 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C39 Si1 C38 110.0(3) . . ?
C39 Si1 C40 110.9(4) . . ?
C38 Si1 C40 110.6(3) . . ?
C39 Si1 C37 110.4(2) . . ?
C38 Si1 C37 107.6(2) . . ?
C40 Si1 C37 107.3(2) . . ?
C12 C11 C16 118.2(3) . . ?
C12 C11 C10 121.1(3) . . ?
C16 C11 C10 120.7(3) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C25 C20 C21 119.0(3) . . ?
C25 C20 N2 118.0(2) . . ?
C21 C20 N2 122.9(3) . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 Cl1 119.7(3) . . ?
C24 C23 Cl1 119.0(3) . . ?
C23 C24 C25 119.1(4) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C20 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C31 C30 C35 120.1(3) . . ?
C31 C30 N1 119.2(3) . . ?
C35 C30 N1 120.8(2) . . ?
C30 C31 C32 120.6(3) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C33 C32 C31 119.8(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 120.3(3) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C33 C34 C35 121.2(3) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C34 C35 C30 118.1(3) . . ?
C34 C35 C36 120.9(3) . . ?
C30 C35 C36 120.9(2) . . ?
C37 C36 C35 178.1(3) . . ?
C36 C37 Si1 175.3(3) . . ?
Si1 C38 H01E 109.5 . . ?
Si1 C38 H38 109.5 . . ?
H01E C38 H38 109.5 . . ?
Si1 C38 H01K 109.5 . . ?
H01E C38 H01K 109.5 . . ?
H38 C38 H01K 109.5 . . ?
Si1 C39 H01O 109.5 . . ?
Si1 C39 H01P 109.5 . . ?
H01O C39 H01P 109.5 . . ?
Si1 C39 H01Q 109.5 . . ?
H01O C39 H01Q 109.5 . . ?
H01P C39 H01Q 109.5 . . ?
Si1 C40 H01L 109.5 . . ?
Si1 C40 H01M 109.5 . . ?
H01L C40 H01M 109.5 . . ?
Si1 C40 H01N 109.5 . . ?
H01L C40 H01N 109.5 . . ?
H01M C40 H01N 109.5 . . ?
C51 C50 C55 119.2(3) . . ?
C51 C50 N3 119.4(3) . . ?
C55 C50 N3 121.4(3) . . ?
C50 C51 C52 120.6(3) . . ?
C50 C51 H51 119.7 . . ?
C52 C51 H51 119.7 . . ?
C53 C52 C51 119.0(4) . . ?
C53 C52 H52 120.5 . . ?
C51 C52 H52 120.5 . . ?
C54 C53 C52 121.2(3) . . ?
C54 C53 Cl2 119.2(3) . . ?
C52 C53 Cl2 119.6(3) . . ?
C53 C54 C55 119.7(3) . . ?
C53 C54 H54 120.1 . . ?
C55 C54 H54 120.1 . . ?
C54 C55 C50 120.3(3) . . ?
C54 C55 H55 119.8 . . ?
C50 C55 H55 119.8 . . ?
N4 C60 C61 113.6(2) . . ?
N4 C60 H00B 108.8 . . ?
C61 C60 H00B 108.8 . . ?
N4 C60 H00C 108.8 . . ?
C61 C60 H00C 108.8 . . ?
H00B C60 H00C 107.7 . . ?
C62 C61 C66 118.2(3) . . ?
C62 C61 C60 121.2(3) . . ?
C66 C61 C60 120.6(3) . . ?
C63 C62 C61 121.4(3) . . ?
C63 C62 H62 119.3 . . ?
C61 C62 H62 119.3 . . ?
C62 C63 C64 119.5(3) . . ?
C62 C63 H63 120.3 . . ?
C64 C63 H63 120.3 . . ?
C65 C64 C63 119.7(3) . . ?
C65 C64 H64 120.1 . . ?
C63 C64 H64 120.1 . . ?
C66 C65 C64 120.5(3) . . ?
C66 C65 H65 119.7 . . ?
C64 C65 H65 119.7 . . ?
C65 C66 C61 120.6(3) . . ?
C65 C66 H66 119.7 . . ?
C61 C66 H66 119.7 . . ?
C71 C70 C75 120.2(2) . . ?
C71 C70 N4 118.3(2) . . ?
C75 C70 N4 121.5(2) . . ?
C72 C71 C70 120.5(3) . . ?
C72 C71 H71 119.8 . . ?
C70 C71 H71 119.8 . . ?
C73 C72 C71 119.9(3) . . ?
C73 C72 H72 120.0 . . ?
C71 C72 H72 120.0 . . ?
C72 C73 C74 120.2(3) . . ?
C72 C73 H73 119.9 . . ?
C74 C73 H73 119.9 . . ?
C73 C74 C75 120.7(3) . . ?
C73 C74 H74 119.6 . . ?
C75 C74 H74 119.6 . . ?
C70 C75 C74 118.4(3) . . ?
C70 C75 C76 121.5(2) . . ?
C74 C75 C76 120.0(3) . . ?
C77 C76 C75 177.2(3) . . ?
C76 C77 Si2 177.9(3) . . ?
C79B Si2 C80B 113.8(4) . . ?
C78A Si2 C79A 113.8(7) . . ?
C78A Si2 C77 113.4(5) . . ?
C79B Si2 C77 108.5(2) . . ?
C80B Si2 C77 108.2(2) . . ?
C79A Si2 C77 103.7(7) . . ?
C78A Si2 C80A 110.5(7) . . ?
C79A Si2 C80A 108.6(7) . . ?
C77 Si2 C80A 106.3(5) . . ?
C79B Si2 C78B 109.4(3) . . ?
C80B Si2 C78B 109.2(4) . . ?
C77 Si2 C78B 107.5(2) . . ?
Si2 C78A H78A 109.5 . . ?
Si2 C78A H78B 109.5 . . ?
H78A C78A H78B 109.5 . . ?
Si2 C78A H78C 109.5 . . ?
H78A C78A H78C 109.5 . . ?
H78B C78A H78C 109.5 . . ?
Si2 C79A H79A 109.5 . . ?
Si2 C79A H79B 109.5 . . ?
H79A C79A H79B 109.5 . . ?
Si2 C79A H79C 109.5 . . ?
H79A C79A H79C 109.5 . . ?
H79B C79A H79C 109.5 . . ?
Si2 C80A H80A 109.5 . . ?
Si2 C80A H80B 109.5 . . ?
H80A C80A H80B 109.5 . . ?
Si2 C80A H80C 109.5 . . ?
H80A C80A H80C 109.5 . . ?
H80B C80A H80C 109.5 . . ?
Si2 C78B H78D 109.5 . . ?
Si2 C78B H78E 109.5 . . ?
H78D C78B H78E 109.5 . . ?
Si2 C78B H78F 109.5 . . ?
H78D C78B H78F 109.5 . . ?
H78E C78B H78F 109.5 . . ?
Si2 C79B H79D 109.5 . . ?
Si2 C79B H79E 109.5 . . ?
H79D C79B H79E 109.5 . . ?
Si2 C79B H79F 109.5 . . ?
H79D C79B H79F 109.5 . . ?
H79E C79B H79F 109.5 . . ?
Si2 C80B H80D 109.5 . . ?
Si2 C80B H80E 109.5 . . ?
H80D C80B H80E 109.5 . . ?
Si2 C80B H80F 109.5 . . ?
H80D C80B H80F 109.5 . . ?
H80E C80B H80F 109.5 . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.053




_publcif_funding_html            
;
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_RM2201_a
_database_code_depnum_ccdc_archive 'CCDC 2163369'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2022-03-30 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3-cyclohexyl-1,1-dipropylurea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H26 N2 O'
_chemical_formula_sum            'C13 H26 N2 O'
_chemical_formula_weight         226.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.5207(4)
_cell_length_b                   9.9632(2)
_cell_length_c                   34.8180(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.771(2)
_cell_angle_gamma                90
_cell_volume                     5728.3(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4923
_cell_measurement_theta_min      5.0560
_cell_measurement_theta_max      72.7030

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.050
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.589
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.513
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10376
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         5.083
_diffrn_reflns_theta_max         72.724
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5488
_reflns_number_gt                4141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelxle, mercury, ORTEP'
_computing_publication_material  publCIF
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0840P)²+2.3026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5488
_refine_ls_number_parameters     319
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1568
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43021(9) 0.38403(11) 0.62272(4) 0.0623(3) Uani 1 1 d . . . . .
O2 O 0.34877(8) 0.88017(11) 0.62851(4) 0.0632(4) Uani 1 1 d . . . . .
N4 N 0.40956(8) 1.08274(14) 0.62781(5) 0.0516(4) Uani 1 1 d . . . . .
N3 N 0.26997(8) 1.06227(14) 0.61758(5) 0.0542(4) Uani 1 1 d . . . . .
N1 N 0.40529(12) 0.60403(16) 0.61310(5) 0.0666(5) Uani 1 1 d . . . . .
C30 C 0.34371(10) 1.00287(15) 0.62447(5) 0.0466(4) Uani 1 1 d . . . . .
C37 C 0.49176(9) 1.02858(16) 0.62815(5) 0.0481(4) Uani 1 1 d . . . . .
H37 H 0.487370 0.930571 0.626894 0.058 Uiso 1 1 calc R U . . .
C10 C 0.41096(11) 0.49425(15) 0.63561(5) 0.0515(4) Uani 1 1 d . . . . .
C17 C 0.41528(12) 0.59995(17) 0.57192(5) 0.0555(4) Uani 1 1 d . . . . .
H17 H 0.439989 0.513702 0.565512 0.067 Uiso 1 1 calc R U . . .
C34 C 0.25929(12) 1.19787(18) 0.60324(6) 0.0630(5) Uani 1 1 d . . . . .
H34A H 0.305458 1.251403 0.611799 0.076 Uiso 1 1 calc R U . . .
H34B H 0.211464 1.236195 0.614422 0.076 Uiso 1 1 calc R U . . .
C38 C 0.53883(12) 1.0631(2) 0.66461(6) 0.0677(5) Uani 1 1 d . . . . .
H38A H 0.510654 1.028321 0.686531 0.081 Uiso 1 1 calc R U . . .
H38B H 0.542372 1.159842 0.667225 0.081 Uiso 1 1 calc R U . . .
C11 C 0.41085(15) 0.3981(2) 0.69983(6) 0.0716(6) Uani 1 1 d . . . . .
H11A H 0.435548 0.433142 0.723392 0.086 Uiso 1 1 calc R U . A 3
H11B H 0.449442 0.337783 0.688420 0.086 Uiso 1 1 calc R U . A 3
C42 C 0.53560(13) 1.0738(2) 0.59332(6) 0.0712(6) Uani 1 1 d . . . . .
H42A H 0.538770 1.171024 0.593188 0.085 Uiso 1 1 calc R U . . .
H42B H 0.505417 1.045892 0.570357 0.085 Uiso 1 1 calc R U . . .
C39 C 0.62440(13) 1.0033(3) 0.66420(7) 0.0781(6) Uani 1 1 d . . . . .
H39A H 0.654523 1.031041 0.687201 0.094 Uiso 1 1 calc R U . . .
H39B H 0.620834 0.906146 0.664373 0.094 Uiso 1 1 calc R U . . .
C40 C 0.66890(13) 1.0480(2) 0.62929(8) 0.0801(7) Uani 1 1 d . . . . .
H40A H 0.721179 1.003775 0.628955 0.096 Uiso 1 1 calc R U . . .
H40B H 0.678177 1.144045 0.630651 0.096 Uiso 1 1 calc R U . . .
C41 C 0.62123(13) 1.0151(3) 0.59275(7) 0.0811(7) Uani 1 1 d . . . . .
H41A H 0.617922 0.918459 0.589759 0.097 Uiso 1 1 calc R U . . .
H41B H 0.649169 1.051045 0.570911 0.097 Uiso 1 1 calc R U . . .
C22 C 0.33556(15) 0.6096(3) 0.55063(7) 0.0867(7) Uani 1 1 d . . . . .
H22A H 0.308489 0.691628 0.558038 0.104 Uiso 1 1 calc R U . . .
H22B H 0.301756 0.534590 0.557749 0.104 Uiso 1 1 calc R U . . .
C35 C 0.25062(17) 1.2076(3) 0.56032(8) 0.0917(8) Uani 1 1 d . . . . .
H35A H 0.204271 1.154699 0.551666 0.110 Uiso 1 1 calc R U . . .
H35B H 0.240045 1.300321 0.553277 0.110 Uiso 1 1 calc R U . . .
C12 C 0.33672(18) 0.3205(3) 0.70939(8) 0.0911(7) Uani 1 1 d . . . . .
H12A H 0.313979 0.279209 0.686240 0.109 Uiso 1 1 calc R U . . .
H12B H 0.296508 0.380996 0.719396 0.109 Uiso 1 1 calc R U . . .
C18 C 0.47097(17) 0.7096(3) 0.55965(8) 0.0938(8) Uani 1 1 d . . . . .
H18A H 0.523916 0.696380 0.571881 0.113 Uiso 1 1 calc R U . . .
H18B H 0.450242 0.795327 0.568186 0.113 Uiso 1 1 calc R U . . .
N2A N 0.39438(12) 0.50938(15) 0.67342(5) 0.0688(5) Uani 0.7932 1 d D . P B 3
C16A C 0.3858(3) 0.8350(5) 0.7301(2) 0.0986(17) Uani 0.7932 1 d D . P B 3
H16A H 0.428256 0.891341 0.740509 0.148 Uiso 0.7932 1 calc R U P B 3
H16B H 0.355403 0.798460 0.750713 0.148 Uiso 0.7932 1 calc R U P B 3
H16C H 0.350608 0.887006 0.713494 0.148 Uiso 0.7932 1 calc R U P B 3
C15A C 0.42282(18) 0.7206(3) 0.70727(8) 0.0711(6) Uani 0.7932 1 d D . P B 3
H15A H 0.454495 0.757717 0.686807 0.085 Uiso 0.7932 1 calc R U P B 3
H15B H 0.458925 0.668831 0.724027 0.085 Uiso 0.7932 1 calc R U P B 3
C14A C 0.35836(14) 0.6299(2) 0.69027(7) 0.0552(5) Uani 0.7932 1 d D . P B 3
H14A H 0.321663 0.603489 0.710136 0.066 Uiso 0.7932 1 calc R U P B 3
H14B H 0.327348 0.678000 0.670582 0.066 Uiso 0.7932 1 calc R U P B 3
N2B N 0.39438(12) 0.50938(15) 0.67342(5) 0.0688(5) Uani 0.2068 1 d D . P B 4
C16B C 0.3551(17) 0.837(2) 0.7270(11) 0.0986(17) Uani 0.2068 1 d D . P B 4
H16D H 0.400553 0.834678 0.744848 0.148 Uiso 0.2068 1 calc R U P B 4
H16E H 0.307178 0.860990 0.740402 0.148 Uiso 0.2068 1 calc R U P B 4
H16F H 0.364701 0.903099 0.707514 0.148 Uiso 0.2068 1 calc R U P B 4
C15B C 0.3438(6) 0.7018(10) 0.7087(3) 0.0711(6) Uani 0.2068 1 d D . P B 4
H15C H 0.302378 0.707911 0.688415 0.085 Uiso 0.2068 1 calc R U P B 4
H15D H 0.325254 0.638867 0.727745 0.085 Uiso 0.2068 1 calc R U P B 4
C14B C 0.4207(6) 0.6496(9) 0.6921(3) 0.0552(5) Uani 0.2068 1 d D . P B 4
H14C H 0.462435 0.637289 0.712013 0.066 Uiso 0.2068 1 calc R U P B 4
H14D H 0.440680 0.710471 0.672796 0.066 Uiso 0.2068 1 calc R U P B 4
C13 C 0.3567(2) 0.2120(3) 0.73908(9) 0.1175(11) Uani 1 1 d . . . . .
H13A H 0.397658 0.153647 0.729485 0.176 Uiso 1 1 calc R U . . .
H13B H 0.308836 0.160891 0.743944 0.176 Uiso 1 1 calc R U . . .
H13C H 0.376187 0.253197 0.762518 0.176 Uiso 1 1 calc R U . . .
C19 C 0.4795(3) 0.7130(4) 0.51618(11) 0.1387(16) Uani 1 1 d . . . . .
H19A H 0.511238 0.790814 0.509300 0.166 Uiso 1 1 calc R U . . .
H19B H 0.508268 0.633468 0.508124 0.166 Uiso 1 1 calc R U . . .
C21 C 0.3451(2) 0.6092(4) 0.50745(8) 0.1224(12) Uani 1 1 d . . . . .
H21A H 0.367514 0.523766 0.499644 0.147 Uiso 1 1 calc R U . . .
H21B H 0.292397 0.619419 0.494733 0.147 Uiso 1 1 calc R U . . .
C36 C 0.3239(2) 1.1601(4) 0.54010(8) 0.1311(14) Uani 1 1 d . . . . .
H36A H 0.369004 1.217268 0.546690 0.197 Uiso 1 1 calc R U . . .
H36B H 0.313482 1.162903 0.512832 0.197 Uiso 1 1 calc R U . . .
H36C H 0.336230 1.069699 0.547800 0.197 Uiso 1 1 calc R U . . .
C20 C 0.3988(4) 0.7189(4) 0.49552(10) 0.1523(19) Uani 1 1 d . . . . .
H20A H 0.373370 0.804443 0.500721 0.183 Uiso 1 1 calc R U . . .
H20B H 0.406515 0.712977 0.468067 0.183 Uiso 1 1 calc R U . . .
C31A C 0.19804(12) 0.9755(2) 0.61557(8) 0.0755(6) Uani 0.4114 1 d D . P C 1
H31A H 0.176790 0.974858 0.589291 0.091 Uiso 0.4114 1 calc R U P C 1
H31B H 0.214538 0.884595 0.621966 0.091 Uiso 0.4114 1 calc R U P C 1
C33A C 0.1596(10) 1.022(2) 0.6826(4) 0.130(3) Uani 0.4114 1 d D . P C 1
H33A H 0.183266 0.938420 0.690408 0.195 Uiso 0.4114 1 calc R U P C 1
H33B H 0.113591 1.041117 0.697855 0.195 Uiso 0.4114 1 calc R U P C 1
H33C H 0.198890 1.092765 0.685980 0.195 Uiso 0.4114 1 calc R U P C 1
C32A C 0.1330(4) 1.0146(7) 0.6408(2) 0.0970(13) Uani 0.4114 1 d D . P C 1
H32A H 0.089236 0.950125 0.638024 0.116 Uiso 0.4114 1 calc R U P C 1
H32B H 0.112182 1.101431 0.632694 0.116 Uiso 0.4114 1 calc R U P C 1
C31B C 0.19804(12) 0.9755(2) 0.61557(8) 0.0755(6) Uani 0.5886 1 d D . P C 2
H31C H 0.211786 0.892248 0.602902 0.091 Uiso 0.5886 1 calc R U P C 2
H31D H 0.156089 1.019381 0.600031 0.091 Uiso 0.5886 1 calc R U P C 2
C33B C 0.1337(6) 1.0651(12) 0.6763(3) 0.130(3) Uani 0.5886 1 d D . P C 2
H33D H 0.178272 1.123964 0.682340 0.195 Uiso 0.5886 1 calc R U P C 2
H33E H 0.108723 1.038125 0.699649 0.195 Uiso 0.5886 1 calc R U P C 2
H33F H 0.094666 1.111039 0.660105 0.195 Uiso 0.5886 1 calc R U P C 2
C32B C 0.1640(3) 0.9426(5) 0.65575(17) 0.0970(13) Uani 0.5886 1 d D . P C 2
H32C H 0.120022 0.878786 0.652578 0.116 Uiso 0.5886 1 calc R U P C 2
H32D H 0.206325 0.900562 0.671508 0.116 Uiso 0.5886 1 calc R U P C 2
H5 H 0.4072(12) 1.163(2) 0.6261(6) 0.056(5) Uiso 1 1 d . . . . .
H7 H 0.3906(13) 0.673(2) 0.6219(6) 0.067(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.232(2) . ?
O2 C30 1.2331(19) . ?
N4 C30 1.350(2) . ?
N4 C37 1.461(2) . ?
N4 H5 0.80(2) . ?
N3 C30 1.369(2) . ?
N3 C34 1.449(2) . ?
N3 C31B 1.469(2) . ?
N3 C31A 1.469(2) . ?
N1 C10 1.347(2) . ?
N1 C17 1.449(2) . ?
N1 H7 0.79(2) . ?
C37 C42 1.501(3) . ?
C37 C38 1.508(3) . ?
C37 H37 0.9800 . ?
C10 N2B 1.361(2) . ?
C10 N2A 1.361(2) . ?
C17 C22 1.494(3) . ?
C17 C18 1.499(3) . ?
C17 H17 0.9800 . ?
C34 C35 1.500(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C38 C39 1.534(3) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C11 N2B 1.461(2) . ?
C11 N2A 1.461(2) . ?
C11 C12 1.494(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C42 C41 1.531(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C39 C40 1.507(3) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.512(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C22 C21 1.517(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C35 C36 1.496(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C12 C13 1.525(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C18 C19 1.525(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N2A C14A 1.470(3) . ?
C16A C15A 1.528(5) . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C15A C14A 1.504(4) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
N2B C14B 1.596(9) . ?
C16B C15B 1.503(14) . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C15B C14B 1.504(11) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C19 C20 1.496(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 C20 1.476(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C31A C32A 1.461(7) . ?
C31A H31A 0.9700 . ?
C31A H31B 0.9700 . ?
C33A C32A 1.508(13) . ?
C33A H33A 0.9600 . ?
C33A H33B 0.9600 . ?
C33A H33C 0.9600 . ?
C32A H32A 0.9700 . ?
C32A H32B 0.9700 . ?
C31B C32B 1.558(5) . ?
C31B H31C 0.9700 . ?
C31B H31D 0.9700 . ?
C33B C32B 1.508(8) . ?
C33B H33D 0.9600 . ?
C33B H33E 0.9600 . ?
C33B H33F 0.9600 . ?
C32B H32C 0.9700 . ?
C32B H32D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C30 N4 C37 121.96(13) . . ?
C30 N4 H5 123.0(14) . . ?
C37 N4 H5 114.3(14) . . ?
C30 N3 C34 124.16(15) . . ?
C30 N3 C31B 117.91(15) . . ?
C34 N3 C31B 116.26(15) . . ?
C30 N3 C31A 117.91(15) . . ?
C34 N3 C31A 116.26(15) . . ?
C10 N1 C17 123.03(15) . . ?
C10 N1 H7 119.6(16) . . ?
C17 N1 H7 116.9(16) . . ?
O2 C30 N4 121.54(15) . . ?
O2 C30 N3 120.36(16) . . ?
N4 C30 N3 118.08(14) . . ?
N4 C37 C42 110.75(14) . . ?
N4 C37 C38 112.18(14) . . ?
C42 C37 C38 111.26(17) . . ?
N4 C37 H37 107.5 . . ?
C42 C37 H37 107.5 . . ?
C38 C37 H37 107.5 . . ?
O1 C10 N1 121.72(17) . . ?
O1 C10 N2B 120.87(15) . . ?
N1 C10 N2B 117.42(15) . . ?
O1 C10 N2A 120.87(15) . . ?
N1 C10 N2A 117.42(15) . . ?
N1 C17 C22 111.30(17) . . ?
N1 C17 C18 110.56(17) . . ?
C22 C17 C18 110.5(2) . . ?
N1 C17 H17 108.1 . . ?
C22 C17 H17 108.1 . . ?
C18 C17 H17 108.1 . . ?
N3 C34 C35 114.24(18) . . ?
N3 C34 H34A 108.7 . . ?
C35 C34 H34A 108.7 . . ?
N3 C34 H34B 108.7 . . ?
C35 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C37 C38 C39 110.79(16) . . ?
C37 C38 H38A 109.5 . . ?
C39 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C39 C38 H38B 109.5 . . ?
H38A C38 H38B 108.1 . . ?
N2B C11 C12 113.3(2) . . ?
N2A C11 C12 113.3(2) . . ?
N2A C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N2A C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C37 C42 C41 111.41(16) . . ?
C37 C42 H42A 109.3 . . ?
C41 C42 H42A 109.3 . . ?
C37 C42 H42B 109.3 . . ?
C41 C42 H42B 109.3 . . ?
H42A C42 H42B 108.0 . . ?
C40 C39 C38 111.44(19) . . ?
C40 C39 H39A 109.3 . . ?
C38 C39 H39A 109.3 . . ?
C40 C39 H39B 109.3 . . ?
C38 C39 H39B 109.3 . . ?
H39A C39 H39B 108.0 . . ?
C39 C40 C41 111.12(18) . . ?
C39 C40 H40A 109.4 . . ?
C41 C40 H40A 109.4 . . ?
C39 C40 H40B 109.4 . . ?
C41 C40 H40B 109.4 . . ?
H40A C40 H40B 108.0 . . ?
C40 C41 C42 111.3(2) . . ?
C40 C41 H41A 109.4 . . ?
C42 C41 H41A 109.4 . . ?
C40 C41 H41B 109.4 . . ?
C42 C41 H41B 109.4 . . ?
H41A C41 H41B 108.0 . . ?
C17 C22 C21 112.0(2) . . ?
C17 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C17 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C36 C35 C34 113.2(2) . . ?
C36 C35 H35A 108.9 . . ?
C34 C35 H35A 108.9 . . ?
C36 C35 H35B 108.9 . . ?
C34 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?
C11 C12 C13 110.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C17 C18 C19 112.0(2) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C10 N2A C11 119.05(15) . . ?
C10 N2A C14A 124.93(16) . . ?
C11 N2A C14A 116.00(17) . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C14A C15A C16A 111.3(3) . . ?
C14A C15A H15A 109.4 . . ?
C16A C15A H15A 109.4 . . ?
C14A C15A H15B 109.4 . . ?
C16A C15A H15B 109.4 . . ?
H15A C15A H15B 108.0 . . ?
N2A C14A C15A 110.9(2) . . ?
N2A C14A H14A 109.5 . . ?
C15A C14A H14A 109.5 . . ?
N2A C14A H14B 109.5 . . ?
C15A C14A H14B 109.5 . . ?
H14A C14A H14B 108.0 . . ?
C10 N2B C11 119.05(15) . . ?
C10 N2B C14B 115.5(4) . . ?
C11 N2B C14B 111.4(4) . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C16B C15B C14B 112.3(15) . . ?
C16B C15B H15C 109.2 . . ?
C14B C15B H15C 109.2 . . ?
C16B C15B H15D 109.2 . . ?
C14B C15B H15D 109.2 . . ?
H15C C15B H15D 107.9 . . ?
C15B C14B N2B 103.6(7) . . ?
C15B C14B H14C 111.0 . . ?
N2B C14B H14C 111.0 . . ?
C15B C14B H14D 111.0 . . ?
N2B C14B H14D 111.0 . . ?
H14C C14B H14D 109.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C20 C19 C18 111.7(3) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C20 C21 C22 111.0(3) . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C21 C20 C19 111.7(3) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C32A C31A N3 115.0(3) . . ?
C32A C31A H31A 108.5 . . ?
N3 C31A H31A 108.5 . . ?
C32A C31A H31B 108.5 . . ?
N3 C31A H31B 108.5 . . ?
H31A C31A H31B 107.5 . . ?
C32A C33A H33A 109.5 . . ?
C32A C33A H33B 109.5 . . ?
H33A C33A H33B 109.5 . . ?
C32A C33A H33C 109.5 . . ?
H33A C33A H33C 109.5 . . ?
H33B C33A H33C 109.5 . . ?
C31A C32A C33A 113.3(7) . . ?
C31A C32A H32A 108.9 . . ?
C33A C32A H32A 108.9 . . ?
C31A C32A H32B 108.9 . . ?
C33A C32A H32B 108.9 . . ?
H32A C32A H32B 107.7 . . ?
N3 C31B C32B 113.2(3) . . ?
N3 C31B H31C 108.9 . . ?
C32B C31B H31C 108.9 . . ?
N3 C31B H31D 108.9 . . ?
C32B C31B H31D 108.9 . . ?
H31C C31B H31D 107.7 . . ?
C32B C33B H33D 109.5 . . ?
C32B C33B H33E 109.5 . . ?
H33D C33B H33E 109.5 . . ?
C32B C33B H33F 109.5 . . ?
H33D C33B H33F 109.5 . . ?
H33E C33B H33F 109.5 . . ?
C33B C32B C31B 113.0(6) . . ?
C33B C32B H32C 109.0 . . ?
C31B C32B H32C 109.0 . . ?
C33B C32B H32D 109.0 . . ?
C31B C32B H32D 109.0 . . ?
H32C C32B H32D 107.8 . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034




_publcif_funding_html            
;
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rm2129d_a
_database_code_depnum_ccdc_archive 'CCDC 2125082'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
# Added during the CSD deposition process: Wednesday 23 March 2022 09:53 AM
# end Validation Reply Form

# start Validation Reply Form
_vrf_PLAT910_rm2129d_a           
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note
RESPONSE: A small number of low angle reflections (12) were obscured by the beam
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.5646(17)
_cell_length_b                   13.0075(10)
_cell_length_c                   8.9569(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.530(8)
_cell_angle_gamma                90
_cell_volume                     2616.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2803
_cell_measurement_theta_min      3.7030
_cell_measurement_theta_max      21.7630

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21848
_diffrn_reflns_av_unetI/netI     0.1010
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.430
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4601
_reflns_number_gt                2157
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    mercury
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4601
_refine_ls_number_parameters     359
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1930
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.13913(11) 0.66121(18) 0.1813(3) 0.0663(7) Uani 1 1 d . . . . .
O1 O 0.37663(10) 0.1562(2) 0.0964(4) 0.0708(8) Uani 1 1 d . . . . .
N4 N 0.17355(14) 0.7350(2) 0.4036(4) 0.0630(9) Uani 1 1 d . . . . .
H4 H 0.1639(16) 0.747(3) 0.493(5) 0.076 Uiso 1 1 d . U . . .
N3 N 0.09807(13) 0.4703(2) 0.5871(4) 0.0624(8) Uani 1 1 d . . . . .
N2 N 0.34596(13) 0.2371(2) 0.3008(4) 0.0678(9) Uani 1 1 d D . . . .
H2 H 0.3604(16) 0.265(3) 0.385(2) 0.081 Uiso 1 1 d D U . . .
N1 N 0.51071(15) 0.1318(2) 0.5141(5) 0.0740(10) Uani 1 1 d . . . . .
C46 C 0.07456(14) 0.5021(3) 0.3420(5) 0.0549(10) Uani 1 1 d . . . . .
C49 C 0.14248(15) 0.6613(3) 0.3202(5) 0.0548(10) Uani 1 1 d . . . . .
C47 C 0.11491(14) 0.5812(3) 0.4029(4) 0.0535(9) Uani 1 1 d . . . . .
C31 C 0.21521(15) 0.8038(3) 0.3488(4) 0.0559(10) Uani 1 1 d . . . . .
C41 C 0.06521(15) 0.4354(3) 0.4610(5) 0.0582(10) Uani 1 1 d . . . . .
C26 C 0.49656(16) 0.1277(2) 0.2618(6) 0.0631(11) Uani 1 1 d . . . . .
C17 C 0.38580(15) 0.1805(3) 0.2294(6) 0.0603(11) Uani 1 1 d . . . . .
C48 C 0.12754(17) 0.5568(3) 0.5513(5) 0.0628(11) Uani 1 1 d . . . . .
C11 C 0.29059(15) 0.2755(3) 0.2350(5) 0.0620(11) Uani 1 1 d . . . . .
C36 C 0.25180(15) 0.7733(3) 0.2420(4) 0.0633(11) Uani 1 1 d . . . . .
H36 H 0.249728 0.706427 0.205130 0.076 Uiso 1 1 calc R U . . .
C32 C 0.22080(16) 0.9020(3) 0.4077(5) 0.0663(11) Uani 1 1 d . . . . .
H32 H 0.197324 0.922483 0.482146 0.080 Uiso 1 1 calc R U . . .
C27 C 0.44121(16) 0.1556(3) 0.3202(6) 0.0630(11) Uani 1 1 d . . . . .
C45 C 0.04619(16) 0.4801(3) 0.2001(5) 0.0704(12) Uani 1 1 d . . . . .
H45 H 0.051667 0.521956 0.118404 0.084 Uiso 1 1 calc R U . . .
C21 C 0.53867(17) 0.1169(3) 0.3858(6) 0.0705(12) Uani 1 1 d . . . . .
C28 C 0.45263(19) 0.1548(3) 0.4722(7) 0.0705(12) Uani 1 1 d . . . . .
C33 C 0.26118(18) 0.9694(3) 0.3558(6) 0.0763(13) Uani 1 1 d . . . . .
H33 H 0.265062 1.035134 0.396436 0.092 Uiso 1 1 calc R U . . .
C12 C 0.25458(16) 0.2203(3) 0.1306(5) 0.0725(12) Uani 1 1 d . . . . .
H12 H 0.266727 0.156195 0.099276 0.087 Uiso 1 1 calc R U . . .
C42 C 0.02843(17) 0.3501(3) 0.4431(6) 0.0730(12) Uani 1 1 d . . . . .
H42 H 0.022890 0.307031 0.523459 0.088 Uiso 1 1 calc R U . . .
C16 C 0.27230(18) 0.3703(3) 0.2825(6) 0.0805(13) Uani 1 1 d . . . . .
H16 H 0.296643 0.408464 0.351543 0.097 Uiso 1 1 calc R U . . .
C35 C 0.29149(16) 0.8425(3) 0.1899(5) 0.0770(13) Uani 1 1 d . . . . .
H35 H 0.315603 0.822022 0.116745 0.092 Uiso 1 1 calc R U . . .
C34 C 0.29575(18) 0.9409(4) 0.2449(6) 0.0812(13) Uani 1 1 d . . . . .
H34 H 0.321739 0.987674 0.207442 0.097 Uiso 1 1 calc R U . . .
C25 C 0.51407(17) 0.1130(3) 0.1182(6) 0.0754(13) Uani 1 1 d . . . . .
H25 H 0.486712 0.118747 0.034102 0.090 Uiso 1 1 calc R U . . .
C50 C 0.10196(18) 0.4219(3) 0.7340(5) 0.0795(12) Uani 1 1 d . . . . .
H50A H 0.123887 0.465660 0.805919 0.119 Uiso 1 1 calc R U . . .
H50B H 0.121967 0.357020 0.729830 0.119 Uiso 1 1 calc R U . . .
H50C H 0.062612 0.411206 0.763267 0.119 Uiso 1 1 calc R U . . .
C43 C 0.00072(18) 0.3312(3) 0.3042(7) 0.0842(14) Uani 1 1 d . . . . .
H43 H -0.024668 0.275061 0.289446 0.101 Uiso 1 1 calc R U . . .
C44 C 0.00986(18) 0.3948(3) 0.1842(6) 0.0844(14) Uani 1 1 d . . . . .
H44 H -0.009116 0.379378 0.090082 0.101 Uiso 1 1 calc R U . . .
C13 C 0.20045(17) 0.2604(4) 0.0726(5) 0.0876(14) Uani 1 1 d . . . . .
H13 H 0.176619 0.223690 0.000734 0.105 Uiso 1 1 calc R U . . .
C14 C 0.1818(2) 0.3536(5) 0.1204(7) 0.1001(17) Uani 1 1 d . . . . .
H14 H 0.145257 0.380202 0.081632 0.120 Uiso 1 1 calc R U . . .
C24 C 0.5731(2) 0.0897(3) 0.1038(7) 0.0954(16) Uani 1 1 d . . . . .
H24 H 0.585584 0.079321 0.008925 0.114 Uiso 1 1 calc R U . . .
C29 C 0.5385(2) 0.1265(3) 0.6678(6) 0.0952(16) Uani 1 1 d . . . . .
H29A H 0.560424 0.063420 0.681888 0.143 Uiso 1 1 calc R U . . .
H29B H 0.508291 0.128967 0.736190 0.143 Uiso 1 1 calc R U . . .
H29C H 0.565119 0.183643 0.686559 0.143 Uiso 1 1 calc R U . . .
C22 C 0.59859(19) 0.0939(3) 0.3720(7) 0.0931(16) Uani 1 1 d . . . . .
H22 H 0.626295 0.087424 0.455341 0.112 Uiso 1 1 calc R U . . .
C23 C 0.6139(2) 0.0818(4) 0.2298(9) 0.1027(19) Uani 1 1 d . . . . .
H23 H 0.653460 0.067488 0.216395 0.123 Uiso 1 1 calc R U . . .
C15 C 0.2171(2) 0.4080(4) 0.2259(7) 0.0978(16) Uani 1 1 d . . . . .
H15 H 0.203989 0.470837 0.259743 0.117 Uiso 1 1 calc R U . . .
H28 H 0.4274(15) 0.164(3) 0.553(5) 0.076(13) Uiso 1 1 d . . . . .
H48 H 0.1558(14) 0.591(3) 0.626(4) 0.067(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C49 1.239(4) . ?
O1 C17 1.231(5) . ?
N4 C49 1.366(5) . ?
N4 C31 1.419(4) . ?
N3 C48 1.361(4) . ?
N3 C41 1.367(5) . ?
N3 C50 1.453(5) . ?
N2 C17 1.367(5) . ?
N2 C11 1.420(4) . ?
N1 C28 1.361(5) . ?
N1 C21 1.376(6) . ?
N1 C29 1.459(6) . ?
C46 C45 1.396(5) . ?
C46 C41 1.405(5) . ?
C46 C47 1.445(5) . ?
C49 C47 1.453(5) . ?
C47 C48 1.369(5) . ?
C31 C36 1.381(5) . ?
C31 C32 1.383(5) . ?
C41 C42 1.386(5) . ?
C26 C25 1.394(6) . ?
C26 C21 1.398(6) . ?
C26 C27 1.446(5) . ?
C17 C27 1.461(5) . ?
C11 C12 1.379(5) . ?
C11 C16 1.381(5) . ?
C36 C35 1.382(5) . ?
C32 C33 1.377(5) . ?
C27 C28 1.361(6) . ?
C45 C44 1.379(5) . ?
C21 C22 1.402(6) . ?
C33 C34 1.372(6) . ?
C12 C13 1.382(5) . ?
C42 C43 1.360(6) . ?
C16 C15 1.387(6) . ?
C35 C34 1.372(6) . ?
C25 C24 1.385(5) . ?
C43 C44 1.387(6) . ?
C13 C14 1.366(6) . ?
C14 C15 1.372(7) . ?
C24 C23 1.391(7) . ?
C22 C23 1.361(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C49 N4 C31 125.1(3) . . ?
C48 N3 C41 108.5(3) . . ?
C48 N3 C50 125.7(4) . . ?
C41 N3 C50 125.8(3) . . ?
C17 N2 C11 126.0(4) . . ?
C28 N1 C21 107.9(4) . . ?
C28 N1 C29 125.8(4) . . ?
C21 N1 C29 126.2(4) . . ?
C45 C46 C41 118.4(3) . . ?
C45 C46 C47 134.9(4) . . ?
C41 C46 C47 106.7(3) . . ?
O2 C49 N4 121.9(3) . . ?
O2 C49 C47 121.6(4) . . ?
N4 C49 C47 116.5(4) . . ?
C48 C47 C46 105.4(3) . . ?
C48 C47 C49 127.0(4) . . ?
C46 C47 C49 127.1(4) . . ?
C36 C31 C32 119.4(3) . . ?
C36 C31 N4 121.3(3) . . ?
C32 C31 N4 119.3(3) . . ?
N3 C41 C42 129.2(4) . . ?
N3 C41 C46 108.2(3) . . ?
C42 C41 C46 122.5(4) . . ?
C25 C26 C21 119.2(4) . . ?
C25 C26 C27 134.4(4) . . ?
C21 C26 C27 106.4(4) . . ?
O1 C17 N2 122.3(3) . . ?
O1 C17 C27 122.5(4) . . ?
N2 C17 C27 115.2(4) . . ?
N3 C48 C47 111.1(4) . . ?
C12 C11 C16 120.0(4) . . ?
C12 C11 N2 122.4(3) . . ?
C16 C11 N2 117.6(4) . . ?
C31 C36 C35 119.8(4) . . ?
C33 C32 C31 119.9(4) . . ?
C28 C27 C26 105.8(4) . . ?
C28 C27 C17 128.9(4) . . ?
C26 C27 C17 125.3(4) . . ?
C44 C45 C46 118.3(4) . . ?
N1 C21 C26 108.5(4) . . ?
N1 C21 C22 128.8(5) . . ?
C26 C21 C22 122.6(5) . . ?
C27 C28 N1 111.2(4) . . ?
C34 C33 C32 120.8(4) . . ?
C11 C12 C13 120.0(4) . . ?
C43 C42 C41 117.9(4) . . ?
C11 C16 C15 119.2(5) . . ?
C34 C35 C36 120.8(4) . . ?
C35 C34 C33 119.2(4) . . ?
C24 C25 C26 118.5(4) . . ?
C42 C43 C44 120.8(4) . . ?
C45 C44 C43 122.1(4) . . ?
C14 C13 C12 120.3(5) . . ?
C13 C14 C15 119.8(4) . . ?
C25 C24 C23 120.5(5) . . ?
C23 C22 C21 116.2(5) . . ?
C22 C23 C24 122.9(5) . . ?
C14 C15 C16 120.7(5) . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_RM2226_a
_database_code_depnum_ccdc_archive 'CCDC 2163367'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2022-03-30 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H5 Cl F5 N O'
_chemical_formula_sum            'C13 H5 Cl F5 N O'
_chemical_formula_weight         321.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.6086(2)
_cell_length_b                   9.3087(3)
_cell_length_c                   23.8205(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.950(3)
_cell_angle_gamma                90
_cell_volume                     1243.47(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2928
_cell_measurement_theta_min      3.6960
_cell_measurement_theta_max      72.6750

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    3.339
_shelx_estimated_absorpt_T_min   0.261
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.239
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4597
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.712
_diffrn_reflns_theta_max         72.797
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2393
_reflns_number_gt                2071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL, ORTEP, Mercury'
_computing_publication_material  publCIF
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+0.2016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2393
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.33392(9) 0.69971(6) 0.49486(2) 0.04085(17) Uani 1 1 d . . . . .
F1 F 0.64212(18) 0.90785(11) 0.20549(5) 0.0341(3) Uani 1 1 d . . . . .
O1 O 0.1415(2) 0.90668(13) 0.24632(5) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.1937(3) 0.68175(15) 0.28198(6) 0.0262(3) Uani 1 1 d . . . . .
H1 H 0.261898 0.598375 0.275514 0.031 Uiso 1 1 calc R U . . .
C1 C 0.2152(3) 0.78264(17) 0.24258(7) 0.0228(3) Uani 1 1 d . . . . .
F2 F 0.8608(2) 0.83345(14) 0.10958(5) 0.0445(3) Uani 1 1 d . . . . .
C2 C 0.3418(3) 0.73377(18) 0.19051(7) 0.0231(4) Uani 1 1 d . . . . .
F3 F 0.6791(2) 0.61880(15) 0.04465(5) 0.0508(4) Uani 1 1 d . . . . .
C3 C 0.5484(3) 0.80319(18) 0.17365(7) 0.0255(4) Uani 1 1 d . . . . .
F4 F 0.2716(2) 0.48268(13) 0.07489(5) 0.0421(3) Uani 1 1 d . . . . .
C4 C 0.6605(3) 0.7651(2) 0.12454(8) 0.0306(4) Uani 1 1 d . . . . .
F5 F 0.05015(18) 0.55838(11) 0.16952(4) 0.0324(3) Uani 1 1 d . . . . .
C5 C 0.5701(3) 0.6568(2) 0.09178(8) 0.0333(4) Uani 1 1 d . . . . .
C6 C 0.3640(3) 0.5861(2) 0.10725(7) 0.0298(4) Uani 1 1 d . . . . .
C7 C 0.2540(3) 0.62586(18) 0.15621(7) 0.0251(4) Uani 1 1 d . . . . .
C9 C 0.1568(3) 0.61953(19) 0.37937(8) 0.0284(4) Uani 1 1 d . . . . .
H9 H 0.299679 0.565376 0.376473 0.034 Uiso 1 1 calc R U . . .
C10 C 0.0346(3) 0.6217(2) 0.42962(8) 0.0307(4) Uani 1 1 d . . . . .
H10 H 0.092897 0.569558 0.461268 0.037 Uiso 1 1 calc R U . . .
C11 C -0.1730(3) 0.70082(19) 0.43281(7) 0.0279(4) Uani 1 1 d . . . . .
C12 C -0.2587(3) 0.77974(19) 0.38780(8) 0.0289(4) Uani 1 1 d . . . . .
H12 H -0.400212 0.834977 0.391074 0.035 Uiso 1 1 calc R U . . .
C13 C -0.1360(3) 0.77761(19) 0.33766(7) 0.0275(4) Uani 1 1 d . . . . .
H13 H -0.193074 0.831550 0.306370 0.033 Uiso 1 1 calc R U . . .
C8 C 0.0708(3) 0.69626(17) 0.33343(7) 0.0233(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7445(17) . ?
F1 C3 1.337(2) . ?
O1 C1 1.230(2) . ?
N1 C1 1.335(2) . ?
N1 C8 1.422(2) . ?
N1 H1 0.8800 . ?
C1 C2 1.509(2) . ?
F2 C4 1.345(2) . ?
C2 C7 1.381(2) . ?
C2 C3 1.392(2) . ?
F3 C5 1.335(2) . ?
C3 C4 1.383(2) . ?
F4 C6 1.333(2) . ?
C4 C5 1.367(3) . ?
F5 C7 1.3469(19) . ?
C5 C6 1.386(3) . ?
C6 C7 1.379(2) . ?
C9 C8 1.387(2) . ?
C9 C10 1.389(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C8 1.390(2) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 126.15(14) . . ?
C1 N1 H1 116.9 . . ?
C8 N1 H1 116.9 . . ?
O1 C1 N1 125.11(15) . . ?
O1 C1 C2 120.36(15) . . ?
N1 C1 C2 114.52(14) . . ?
C7 C2 C3 117.24(15) . . ?
C7 C2 C1 122.52(14) . . ?
C3 C2 C1 120.15(15) . . ?
F1 C3 C4 119.10(15) . . ?
F1 C3 C2 119.75(15) . . ?
C4 C3 C2 121.15(17) . . ?
F2 C4 C5 120.07(17) . . ?
F2 C4 C3 119.77(18) . . ?
C5 C4 C3 120.15(16) . . ?
F3 C5 C4 120.33(18) . . ?
F3 C5 C6 119.55(18) . . ?
C4 C5 C6 120.12(16) . . ?
F4 C6 C7 120.53(16) . . ?
F4 C6 C5 120.50(16) . . ?
C7 C6 C5 118.96(17) . . ?
F5 C7 C6 117.85(16) . . ?
F5 C7 C2 119.73(14) . . ?
C6 C7 C2 122.39(16) . . ?
C8 C9 C10 120.14(16) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 118.93(16) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 121.63(16) . . ?
C12 C11 Cl1 118.89(14) . . ?
C10 C11 Cl1 119.47(14) . . ?
C11 C12 C13 119.32(16) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C8 119.75(16) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C9 C8 C13 120.21(16) . . ?
C9 C8 N1 117.63(15) . . ?
C13 C8 N1 122.07(15) . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.069




_publcif_funding_html            
;
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_RM2231b_a
_database_code_depnum_ccdc_archive 'CCDC 2167662'
loop_
_audit_author_name
_audit_author_address
'Yara van Ingen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Cl N3 O2'
_chemical_formula_sum            'C23 H18 Cl N3 O2'
_chemical_formula_weight         403.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7822(3)
_cell_length_b                   12.3852(6)
_cell_length_c                   27.1093(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1941.40(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2715
_cell_measurement_theta_min      3.9040
_cell_measurement_theta_max      72.8330

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.662
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    1.946
_shelx_estimated_absorpt_T_min   0.359
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7005
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.924
_diffrn_reflns_theta_max         72.942
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3727
_reflns_number_gt                3132
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXL, Mercury, ORTEP'
_computing_publication_material  publCIF
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1039P)²+0.0585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3727
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1829
_refine_ls_wR_factor_gt          0.1709
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1680(7) 0.5729(3) 0.31635(14) 0.0615(10) Uani 1 1 d . . . . .
N1 N 0.3349(8) 0.6104(3) 0.39038(15) 0.0491(10) Uani 1 1 d . . . . .
H1 H 0.445217 0.590489 0.409623 0.059 Uiso 1 1 calc R U . . .
C1 C 0.3097(9) 0.5543(4) 0.34814(18) 0.0444(10) Uani 1 1 d . . . . .
Cl1 Cl -0.2200(3) 0.97324(12) 0.46776(7) 0.0766(5) Uani 1 1 d . . . . .
O2 O 0.6829(7) 0.4895(3) 0.41233(13) 0.0585(10) Uani 1 1 d . . . . .
N2 N 0.4717(7) 0.4683(3) 0.34112(14) 0.0434(9) Uani 1 1 d . . . . .
C2 C 0.6372(8) 0.4343(4) 0.37589(17) 0.0427(10) Uani 1 1 d . . . . .
N3 N 0.8595(8) 0.1629(3) 0.34771(17) 0.0511(10) Uani 1 1 d . . . . .
C3 C 0.7577(8) 0.3313(3) 0.36948(17) 0.0417(10) Uani 1 1 d . . . . .
C4 C 0.7084(9) 0.2434(4) 0.33925(19) 0.0493(11) Uani 1 1 d . . . . .
H4 H 0.588255 0.240739 0.316464 0.059 Uiso 1 1 calc R U . . .
C5 C 1.0141(9) 0.1944(4) 0.38392(18) 0.0457(11) Uani 1 1 d . . . . .
C6 C 0.9555(8) 0.2994(4) 0.39851(16) 0.0402(10) Uani 1 1 d . . . . .
C7 C 1.0903(9) 0.3490(4) 0.43483(19) 0.0478(11) Uani 1 1 d . . . . .
H7 H 1.055728 0.418444 0.445636 0.057 Uiso 1 1 calc R U . . .
C8 C 1.2761(10) 0.2931(4) 0.4544(2) 0.0559(13) Uani 1 1 d . . . . .
H8 H 1.368104 0.326030 0.478223 0.067 Uiso 1 1 calc R U . . .
C9 C 1.3277(11) 0.1884(5) 0.4392(2) 0.0613(14) Uani 1 1 d . . . . .
H9 H 1.450712 0.151981 0.453779 0.074 Uiso 1 1 calc R U . . .
C10 C 1.2010(11) 0.1379(4) 0.4032(2) 0.0565(13) Uani 1 1 d . . . . .
H10 H 1.238363 0.068909 0.392241 0.068 Uiso 1 1 calc R U . . .
C12 C 0.2663(9) 0.3510(4) 0.28328(19) 0.0514(12) Uani 1 1 d . . . . .
H12 H 0.140958 0.348256 0.304745 0.062 Uiso 1 1 calc R U . . .
C13 C 0.2646(10) 0.2909(5) 0.2406(2) 0.0586(13) Uani 1 1 d . . . . .
H13 H 0.137838 0.247756 0.233028 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4527(11) 0.2949(5) 0.2088(2) 0.0600(14) Uani 1 1 d . . . . .
H14 H 0.454763 0.251882 0.180654 0.072 Uiso 1 1 calc R U . . .
C15 C 0.6360(11) 0.3624(5) 0.2188(2) 0.0615(15) Uani 1 1 d . . . . .
H15 H 0.759396 0.366569 0.196825 0.074 Uiso 1 1 calc R U . . .
C16 C 0.6372(9) 0.4239(4) 0.26129(19) 0.0483(11) Uani 1 1 d . . . . .
H16 H 0.759185 0.470676 0.267843 0.058 Uiso 1 1 calc R U . . .
C17 C 0.4538(8) 0.4150(4) 0.29412(17) 0.0421(10) Uani 1 1 d . . . . .
C18 C 0.1995(8) 0.6982(4) 0.40627(17) 0.0420(10) Uani 1 1 d . . . . .
C19 C 0.2856(9) 0.7617(4) 0.44408(19) 0.0497(11) Uani 1 1 d . . . . .
H19 H 0.430392 0.745971 0.457189 0.060 Uiso 1 1 calc R U . . .
C20 C 0.1614(10) 0.8482(4) 0.46289(19) 0.0518(12) Uani 1 1 d . . . . .
H20 H 0.222496 0.890884 0.487941 0.062 Uiso 1 1 calc R U . . .
C21 C -0.0544(10) 0.8696(4) 0.4437(2) 0.0509(12) Uani 1 1 d . . . . .
C22 C -0.1418(10) 0.8085(4) 0.4057(2) 0.0534(12) Uani 1 1 d . . . . .
H22 H -0.285964 0.825171 0.392505 0.064 Uiso 1 1 calc R U . . .
C23 C -0.0180(9) 0.7224(4) 0.3867(2) 0.0491(11) Uani 1 1 d . . . . .
H23 H -0.078934 0.681055 0.361243 0.059 Uiso 1 1 calc R U . . .
C24 C 0.8617(15) 0.0603(5) 0.3209(3) 0.080(2) Uani 1 1 d . . . . .
H24A H 0.767968 0.066493 0.291810 0.119 Uiso 1 1 calc R U . . .
H24B H 0.801029 0.004260 0.341669 0.119 Uiso 1 1 calc R U . . .
H24C H 1.017534 0.042845 0.311655 0.119 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.211(6) . ?
N1 C1 1.347(6) . ?
N1 C18 1.408(6) . ?
N1 H1 0.8600 . ?
C1 N2 1.431(6) . ?
Cl1 C21 1.729(5) . ?
O2 C2 1.230(6) . ?
N2 C2 1.407(6) . ?
N2 C17 1.438(6) . ?
C2 C3 1.464(7) . ?
N3 C4 1.345(6) . ?
N3 C5 1.384(7) . ?
N3 C24 1.464(7) . ?
C3 C4 1.392(7) . ?
C3 C6 1.443(6) . ?
C4 H4 0.9300 . ?
C5 C10 1.390(7) . ?
C5 C6 1.401(7) . ?
C6 C7 1.398(7) . ?
C7 C8 1.384(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 C17 1.375(7) . ?
C12 C13 1.376(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(7) . ?
C16 H16 0.9300 . ?
C18 C19 1.385(7) . ?
C18 C23 1.397(7) . ?
C19 C20 1.387(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(8) . ?
C22 C23 1.382(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C18 126.8(4) . . ?
C1 N1 H1 116.6 . . ?
C18 N1 H1 116.6 . . ?
O1 C1 N1 125.4(5) . . ?
O1 C1 N2 119.3(4) . . ?
N1 C1 N2 115.2(4) . . ?
C2 N2 C1 125.3(4) . . ?
C2 N2 C17 120.3(4) . . ?
C1 N2 C17 114.4(4) . . ?
O2 C2 N2 121.2(4) . . ?
O2 C2 C3 118.5(4) . . ?
N2 C2 C3 120.3(4) . . ?
C4 N3 C5 109.4(4) . . ?
C4 N3 C24 124.4(5) . . ?
C5 N3 C24 126.2(5) . . ?
C4 C3 C6 105.6(4) . . ?
C4 C3 C2 130.8(4) . . ?
C6 C3 C2 123.4(4) . . ?
N3 C4 C3 110.2(4) . . ?
N3 C4 H4 124.9 . . ?
C3 C4 H4 124.9 . . ?
N3 C5 C10 128.8(5) . . ?
N3 C5 C6 107.8(4) . . ?
C10 C5 C6 123.3(5) . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 C3 134.9(4) . . ?
C5 C6 C3 107.0(4) . . ?
C8 C7 C6 118.9(5) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 121.4(5) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C5 117.0(5) . . ?
C9 C10 H10 121.5 . . ?
C5 C10 H10 121.5 . . ?
C17 C12 C13 119.8(5) . . ?
C17 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.2(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.2(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 120.7(5) . . ?
C12 C17 N2 120.7(4) . . ?
C16 C17 N2 118.5(5) . . ?
C19 C18 C23 118.8(5) . . ?
C19 C18 N1 117.7(4) . . ?
C23 C18 N1 123.4(5) . . ?
C18 C19 C20 121.6(5) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 118.6(5) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 Cl1 119.3(4) . . ?
C20 C21 Cl1 120.1(4) . . ?
C21 C22 C23 120.8(5) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 119.4(5) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.058




_publcif_funding_html            
;
;
