# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_20190717HU_LWF_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1941459'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2020-09-10 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         ?
_chemical_formula_sum            'C18 H14 Cl N O'
_chemical_formula_weight         295.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1789(9)
_cell_length_b                   8.6698(11)
_cell_length_c                   24.751(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1540.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      59.88

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.429
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20404
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.107
_diffrn_reflns_theta_max         52.998
_diffrn_reflns_theta_full        52.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2719
_reflns_number_gt                1853
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0874
_refine_ls_wR_factor_ref         0.1863
_refine_ls_wR_factor_gt          0.1737
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.006

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
C1 C 0.4634(15) 0.5253(13) 0.2522(3) 0.101(3) Uani 1 1 d . . . . .
H1 H 0.568764 0.591025 0.249318 0.121 Uiso 1 1 calc R U . . .
C2 C 0.3405(19) 0.5126(16) 0.2090(3) 0.121(4) Uani 1 1 d . . . . .
H2 H 0.363890 0.567960 0.176606 0.145 Uiso 1 1 calc R U . . .
C3 C 0.1886(18) 0.4221(16) 0.2129(4) 0.115(4) Uani 1 1 d . . . . .
C4 C 0.1575(16) 0.3449(13) 0.2596(4) 0.107(3) Uani 1 1 d . . . . .
H4 H 0.050461 0.280899 0.262452 0.129 Uiso 1 1 calc R U . . .
C5 C 0.2749(13) 0.3561(11) 0.3028(3) 0.085(3) Uani 1 1 d . . . . .
H5 H 0.246438 0.303270 0.335366 0.102 Uiso 1 1 calc R U . . .
C6 C 0.4337(13) 0.4432(12) 0.2993(3) 0.082(2) Uani 1 1 d . . . . .
C7 C 0.5617(12) 0.4596(10) 0.3454(3) 0.074(2) Uani 1 1 d . . . . .
C8 C 0.7485(13) 0.4687(12) 0.3409(3) 0.096(3) Uani 1 1 d . . . . .
H8 H 0.799368 0.462939 0.305569 0.115 Uiso 1 1 calc R U . . .
C9 C 0.8823(13) 0.4870(15) 0.3865(3) 0.124(4) Uani 1 1 d . . . . .
H9A H 0.813982 0.513024 0.419527 0.185 Uiso 1 1 calc R U . . .
H9B H 0.970544 0.569804 0.378019 0.185 Uiso 1 1 calc R U . . .
H9C H 0.950404 0.390264 0.391853 0.185 Uiso 1 1 calc R U . . .
C10 C 0.4719(13) 0.3130(13) 0.4257(3) 0.086(3) Uani 1 1 d . . . . .
C11 C 0.3768(13) 0.3159(14) 0.4769(3) 0.099(3) Uani 1 1 d . . . . .
H11 H 0.368037 0.223364 0.497290 0.118 Uiso 1 1 calc R U . . .
C12 C 0.2983(13) 0.4485(16) 0.4972(3) 0.103(3) Uani 1 1 d . . . . .
H12 H 0.238013 0.445740 0.531333 0.124 Uiso 1 1 calc R U . . .
C13 C 0.3056(12) 0.5870(13) 0.4685(3) 0.082(3) Uani 1 1 d . . . . .
C14 C 0.2318(13) 0.7238(15) 0.4889(4) 0.099(3) Uani 1 1 d . . . . .
H14 H 0.169282 0.722239 0.522716 0.118 Uiso 1 1 calc R U . . .
C15 C 0.2466(14) 0.8592(15) 0.4618(4) 0.109(3) Uani 1 1 d . . . . .
H15 H 0.194172 0.950813 0.476283 0.130 Uiso 1 1 calc R U . . .
C16 C 0.3408(12) 0.8624(12) 0.4117(4) 0.092(3) Uani 1 1 d . . . . .
H16 H 0.354508 0.957445 0.393014 0.111 Uiso 1 1 calc R U . . .
C17 C 0.4123(11) 0.7307(11) 0.3900(3) 0.077(2) Uani 1 1 d . . . . .
H17 H 0.469848 0.732978 0.355406 0.093 Uiso 1 1 calc R U . . .
C18 C 0.4006(10) 0.5934(11) 0.4185(3) 0.075(2) Uani 1 1 d . . . . .
Cl1 Cl 0.0369(5) 0.4109(6) 0.15925(12) 0.186(2) Uani 1 1 d . . . . .
N1 N 0.4744(9) 0.4545(9) 0.3980(2) 0.0756(18) Uani 1 1 d . . . . .
O1 O 0.5418(11) 0.1994(8) 0.4057(2) 0.108(2) 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
C1 C2 1.390(13) . ?
C1 C6 1.383(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.347(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.356(14) . ?
C3 Cl1 1.720(9) . ?
C4 C5 1.364(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.471(10) . ?
C7 C8 1.348(11) . ?
C7 N1 1.447(9) . ?
C8 C9 1.490(11) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O1 1.212(10) . ?
C10 C11 1.439(11) . ?
C10 N1 1.405(11) . ?
C11 C12 1.375(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(13) . ?
C13 C18 1.415(10) . ?
C14 C15 1.356(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.411(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.363(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(11) . ?
C17 H17 0.9500 . ?
C18 N1 1.410(10) . ?

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
C2 C1 C6 120.7(10) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.3(10) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 118.8(9) . . ?
C2 C3 Cl1 119.4(10) . . ?
C4 C3 Cl1 121.8(11) . . ?
C5 C4 C3 122.1(11) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 120.3(9) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 117.7(8) . . ?
C1 C6 C7 120.5(9) . . ?
C5 C6 C7 121.7(7) . . ?
C8 C7 N1 120.4(7) . . ?
C8 C7 C6 124.3(7) . . ?
N1 C7 C6 115.1(7) . . ?
C7 C8 C9 125.9(8) . . ?
C7 C8 H8 117.0 . . ?
C9 C8 H8 117.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C11 124.8(10) . . ?
O1 C10 N1 120.4(8) . . ?
C11 C10 N1 114.8(9) . . ?
C12 C11 C10 122.0(10) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 121.2(8) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C18 117.8(10) . . ?
C14 C13 C12 122.3(8) . . ?
C18 C13 C12 119.8(9) . . ?
C15 C14 C13 121.9(9) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 119.3(11) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.7(10) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.7(8) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 120.6(9) . . ?
C17 C18 N1 121.8(6) . . ?
C13 C18 N1 117.5(8) . . ?
C7 N1 C10 118.1(7) . . ?
C7 N1 C18 117.4(7) . . ?
C10 N1 C18 124.4(6) . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_20191017ZH_LMF_2KL_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1960857'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2020-09-10 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         ?
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.9647(3)
_cell_length_b                   9.7465(4)
_cell_length_c                   9.2350(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.2250(10)
_cell_angle_gamma                90
_cell_volume                     757.15(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      3.95
_cell_measurement_theta_max      53.96

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.420
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12804
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         9.085
_diffrn_reflns_theta_max         53.959
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2691
_reflns_number_gt                2666
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.970

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0491P)²+0.0332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(7)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2691
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
C1 C 0.54469(19) 0.32519(17) 0.08426(18) 0.0408(4) Uani 1 1 d . . . . .
H1 H 0.488280 0.245704 0.035242 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6874(2) 0.3591(2) 0.0658(2) 0.0500(4) Uani 1 1 d . . . . .
H2 H 0.728921 0.302028 0.005446 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7686(2) 0.4746(2) 0.1342(2) 0.0548(5) Uani 1 1 d . . . . .
H3 H 0.865658 0.498040 0.120265 0.066 Uiso 1 1 calc R U . . .
C4 C 0.7096(2) 0.5566(2) 0.2229(2) 0.0540(4) Uani 1 1 d . . . . .
H4 H 0.765696 0.636884 0.269717 0.065 Uiso 1 1 calc R U . . .
C5 C 0.56847(19) 0.52234(17) 0.24421(19) 0.0420(4) Uani 1 1 d . . . . .
H5 H 0.529340 0.578394 0.307323 0.050 Uiso 1 1 calc R U . . .
C6 C 0.48404(18) 0.40657(16) 0.17381(16) 0.0336(3) Uani 1 1 d . . . . .
C7 C 0.32861(18) 0.36981(16) 0.19096(17) 0.0345(3) Uani 1 1 d . . . . .
C8 C 0.2835(2) 0.22583(18) 0.20684(19) 0.0426(4) Uani 1 1 d . . . . .
H8 H 0.366677 0.155924 0.211420 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1636(2) 0.1822(2) 0.2774(2) 0.0550(5) Uani 1 1 d . . . . .
H9A H 0.097981 0.261077 0.282861 0.083 Uiso 1 1 calc R U . . .
H9B H 0.218670 0.146767 0.381587 0.083 Uiso 1 1 calc R U . . .
H9C H 0.095723 0.110164 0.213854 0.083 Uiso 1 1 calc R U . . .
C10 C 0.28939(18) 0.48947(16) 0.41163(17) 0.0352(3) Uani 1 1 d . . . . .
C11 C 0.3919(2) 0.39739(17) 0.51480(18) 0.0424(4) Uani 1 1 d . . . . .
H11 H 0.446343 0.329459 0.478495 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4134(2) 0.4060(2) 0.6705(2) 0.0503(4) Uani 1 1 d . . . . .
H12 H 0.482509 0.342832 0.740404 0.060 Uiso 1 1 calc R U . . .
C13 C 0.3365(3) 0.5043(2) 0.7260(2) 0.0540(5) Uani 1 1 d . . . . .
H13 H 0.348529 0.506203 0.832303 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2426(2) 0.5991(2) 0.6263(2) 0.0477(4) Uani 1 1 d . . . . .
H14 H 0.192557 0.668567 0.665327 0.057 Uiso 1 1 calc R U . . .
C15 C 0.21837(18) 0.59619(17) 0.46726(18) 0.0384(3) Uani 1 1 d . . . . .
C16 C 0.12674(18) 0.69975(17) 0.3607(2) 0.0424(4) Uani 1 1 d . . . . .
C17 C 0.10999(19) 0.69034(19) 0.2108(2) 0.0440(4) Uani 1 1 d . . . . .
H17 H 0.050796 0.759525 0.142532 0.053 Uiso 1 1 calc R U . . .
C18 C 0.17731(17) 0.58042(18) 0.14779(18) 0.0388(3) Uani 1 1 d . . . . .
C19 C 0.0545(3) 0.8174(2) 0.4182(3) 0.0611(5) Uani 1 1 d . . . . .
H19A H -0.002502 0.877316 0.331523 0.092 Uiso 1 1 calc R U . . .
H19B H 0.138787 0.869706 0.494706 0.092 Uiso 1 1 calc R U . . .
H19C H -0.019778 0.781986 0.465937 0.092 Uiso 1 1 calc R U . . .
N1 N 0.25776(15) 0.47875(13) 0.25226(14) 0.0344(3) Uani 1 1 d . . . . .
O1 O 0.22049(14) 0.29885(13) 0.06287(12) 0.0446(3) Uani 1 1 d . . . . .
O2 O 0.16725(15) 0.57266(14) 0.01205(13) 0.0512(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
C1 C6 1.385(2) . ?
C1 C2 1.388(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(2) . ?
C7 O1 1.4228(18) . ?
C7 N1 1.449(2) . ?
C7 C8 1.482(2) . ?
C8 O1 1.440(2) . ?
C8 C9 1.498(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.397(2) . ?
C10 N1 1.4031(18) . ?
C10 C15 1.406(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.369(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.408(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.450(2) . ?
C16 C17 1.343(3) . ?
C16 C19 1.501(2) . ?
C17 C18 1.447(2) . ?
C17 H17 0.9500 . ?
C18 O2 1.228(2) . ?
C18 N1 1.397(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C6 C1 C2 120.37(16) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.31(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.95(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.21(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.34(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.81(14) . . ?
C1 C6 C7 119.81(14) . . ?
C5 C6 C7 121.38(14) . . ?
O1 C7 N1 114.60(13) . . ?
O1 C7 C8 59.41(10) . . ?
N1 C7 C8 118.94(13) . . ?
O1 C7 C6 114.79(13) . . ?
N1 C7 C6 114.52(13) . . ?
C8 C7 C6 122.15(14) . . ?
O1 C8 C7 58.26(10) . . ?
O1 C8 C9 115.48(15) . . ?
C7 C8 C9 124.98(16) . . ?
O1 C8 H8 115.1 . . ?
C7 C8 H8 115.1 . . ?
C9 C8 H8 115.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 120.95(14) . . ?
C11 C10 C15 120.00(14) . . ?
N1 C10 C15 119.04(14) . . ?
C12 C11 C10 119.46(16) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 121.30(18) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.28(16) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.70(17) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 117.99(16) . . ?
C14 C15 C16 122.73(16) . . ?
C10 C15 C16 119.26(14) . . ?
C17 C16 C15 119.15(15) . . ?
C17 C16 C19 120.56(17) . . ?
C15 C16 C19 120.27(16) . . ?
C16 C17 C18 123.48(16) . . ?
C16 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
O2 C18 N1 119.98(15) . . ?
O2 C18 C17 124.24(15) . . ?
N1 C18 C17 115.78(14) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 N1 C10 122.71(13) . . ?
C18 N1 C7 116.18(12) . . ?
C10 N1 C7 120.49(12) . . ?
C7 O1 C8 62.33(10) . . ?

_refine_diff_density_max         0.116
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.022

