# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2269832'
loop_
_audit_author_name
_audit_author_address
'Takuya Shimbayashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2023-06-14 deposited with the CCDC.	2023-09-08 downloaded from the CCDC.
;
_audit_creation_date             2020-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
1-(adamantan-1-yl)-2-methyl-4-phenyl-1H-pyrrole
_chemical_formula_moiety         'C21 H25 N'
_chemical_formula_sum            'C21 H25 N'
_chemical_formula_weight         291.42
_chemical_melting_point          347-348
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.960(10)
_cell_length_b                   14.289(14)
_cell_length_c                   12.521(13)
_cell_angle_alpha                90
_cell_angle_beta                 113.237(12)
_cell_angle_gamma                90
_cell_volume                     1637(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    168.15
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1558
_diffrn_reflns_av_unetI/netI     0.1656
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12777
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.375
_diffrn_reflns_theta_min         3.347
_diffrn_ambient_temperature      168.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            Mo
_diffrn_source_type              'Sealed Tube'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1629
_reflns_number_total             3613
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1983
_refine_ls_R_factor_gt           0.0907
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00G), C00E(H00J), C00H(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C008(H00C,H00D), C00A(H00E,H00F), C00D(H00H,H00I), C00G(H00L,
 H00M), C00K(H00Q,H00R)
2.c Aromatic/amide H refined with riding coordinates:
 C002(H002), C006(H006), C009(H009), C00F(H00K), C00I(H00O), C00J(H00P),
 C00M(H00V)
2.d Idealised Me refined as rotating group:
 C00L(H00S,H00T,H00U)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N001 N 0.8092(3) 0.5156(2) 0.5797(2) 0.0278(7) Uani 1 1 d . . . . .
C002 C 0.7868(3) 0.5981(2) 0.5164(3) 0.0262(8) Uani 1 1 d . . . . .
H002 H 0.739904 0.602214 0.434149 0.031 Uiso 1 1 calc R . . . .
C003 C 0.8402(3) 0.7729(2) 0.5576(3) 0.0262(8) Uani 1 1 d . . . . .
C004 C 0.7552(4) 0.4212(2) 0.5283(3) 0.0262(8) Uani 1 1 d . . . . .
C005 C 0.8425(3) 0.6733(2) 0.5900(3) 0.0266(8) Uani 1 1 d . . . . .
C006 C 0.7715(4) 0.8965(3) 0.4119(3) 0.0337(9) Uani 1 1 d . . . . .
H006 H 0.725806 0.914723 0.332659 0.040 Uiso 1 1 calc R . . . .
C007 C 0.8819(4) 0.3499(2) 0.5600(3) 0.0309(9) Uani 1 1 d . . . . .
H00A H 0.955363 0.372405 0.531073 0.037 Uiso 1 1 calc R . . . .
H00B H 0.930155 0.343466 0.645550 0.037 Uiso 1 1 calc R . . . .
C008 C 0.6389(3) 0.3847(2) 0.5714(3) 0.0293(9) Uani 1 1 d . . . . .
H00C H 0.683031 0.378499 0.657117 0.035 Uiso 1 1 calc R . . . .
H00D H 0.557449 0.430044 0.550585 0.035 Uiso 1 1 calc R . . . .
C009 C 0.9019(3) 0.6342(3) 0.7049(3) 0.0322(9) Uani 1 1 d . . . . .
H009 H 0.948488 0.668663 0.774823 0.039 Uiso 1 1 calc R . . . .
C00A C 0.6832(4) 0.4293(2) 0.3943(3) 0.0296(9) Uani 1 1 d . . . . .
H00E H 0.601282 0.474520 0.371743 0.036 Uiso 1 1 calc R . . . .
H00F H 0.755601 0.452911 0.364838 0.036 Uiso 1 1 calc R . . . .
C00B C 0.8807(4) 0.5388(3) 0.6976(3) 0.0309(9) Uani 1 1 d . . . . .
C00C C 0.6256(4) 0.3330(2) 0.3395(3) 0.0306(9) Uani 1 1 d . . . . .
H00G H 0.578887 0.339601 0.253031 0.037 Uiso 1 1 calc R . . . .
C00D C 0.7082(4) 0.2190(2) 0.5505(3) 0.0333(9) Uani 1 1 d . . . . .
H00H H 0.754169 0.212508 0.636106 0.040 Uiso 1 1 calc R . . . .
H00I H 0.671043 0.156891 0.516775 0.040 Uiso 1 1 calc R . . . .
C00E C 0.5802(4) 0.2895(2) 0.5165(3) 0.0291(9) Uani 1 1 d . . . . .
H00J H 0.506013 0.266571 0.545653 0.035 Uiso 1 1 calc R . . . .
C00F C 0.7749(4) 0.8024(2) 0.4417(3) 0.0318(9) Uani 1 1 d . . . . .
H00K H 0.732052 0.757232 0.382240 0.038 Uiso 1 1 calc R . . . .
C00G C 0.7519(4) 0.2629(3) 0.3718(3) 0.0340(10) Uani 1 1 d . . . . .
H00L H 0.825416 0.285032 0.342682 0.041 Uiso 1 1 calc R . . . .
H00M H 0.715008 0.201253 0.336229 0.041 Uiso 1 1 calc R . . . .
C00H C 0.8217(4) 0.2539(2) 0.5050(3) 0.0306(9) Uani 1 1 d . . . . .
H00N H 0.904063 0.207989 0.527202 0.037 Uiso 1 1 calc R . . . .
C00I C 0.8346(4) 0.9644(3) 0.4973(3) 0.0386(10) Uani 1 1 d . . . . .
H00O H 0.832651 1.028639 0.477243 0.046 Uiso 1 1 calc R . . . .
C00J C 0.9039(4) 0.8415(3) 0.6415(3) 0.0371(10) Uani 1 1 d . . . . .
H00P H 0.951009 0.823681 0.720778 0.045 Uiso 1 1 calc R . . . .
C00K C 0.5099(4) 0.2989(3) 0.3849(3) 0.0331(9) Uani 1 1 d . . . . .
H00Q H 0.428196 0.344150 0.362613 0.040 Uiso 1 1 calc R . . . .
H00R H 0.470230 0.237607 0.349564 0.040 Uiso 1 1 calc R . . . .
C00L C 0.9309(4) 0.4737(3) 0.7996(3) 0.0431(11) Uani 1 1 d . . . . .
H00S H 0.848939 0.434320 0.796878 0.065 Uiso 1 1 calc GR . . . .
H00T H 0.966726 0.510139 0.871761 0.065 Uiso 1 1 calc GR . . . .
H00U H 1.009699 0.433910 0.797035 0.065 Uiso 1 1 calc GR . . . .
C00M C 0.8999(4) 0.9356(3) 0.6116(4) 0.0450(11) Uani 1 1 d . . . . .
H00V H 0.942889 0.980873 0.670952 0.054 Uiso 1 1 calc R . . . .


_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
N001 C002 1.389(4) . ?
N001 C004 1.500(4) . ?
N001 C00B 1.402(4) . ?
C002 C005 1.382(5) . ?
C003 C005 1.477(5) . ?
C003 C00F 1.400(5) . ?
C003 C00J 1.394(5) . ?
C004 C007 1.547(5) . ?
C004 C008 1.549(5) . ?
C004 C00A 1.547(5) . ?
C005 C009 1.435(5) . ?
C006 C00F 1.393(5) . ?
C006 C00I 1.395(5) . ?
C007 C00H 1.546(5) . ?
C008 C00E 1.532(5) . ?
C009 C00B 1.378(5) . ?
C00A C00C 1.543(5) . ?
C00B C00L 1.499(5) . ?
C00C C00G 1.533(5) . ?
C00C C00K 1.551(5) . ?
C00D C00E 1.546(5) . ?
C00D C00H 1.537(5) . ?
C00E C00K 1.521(5) . ?
C00G C00H 1.538(5) . ?
C00I C00M 1.381(5) . ?
C00J C00M 1.392(5) . ?

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
C002 N001 C004 124.6(3) . . ?
C002 N001 C00B 107.5(3) . . ?
C00B N001 C004 127.7(3) . . ?
C005 C002 N001 110.3(3) . . ?
C00F C003 C005 121.7(3) . . ?
C00J C003 C005 121.1(3) . . ?
C00J C003 C00F 117.2(3) . . ?
N001 C004 C007 111.3(3) . . ?
N001 C004 C008 110.2(3) . . ?
N001 C004 C00A 109.4(3) . . ?
C007 C004 C008 109.5(3) . . ?
C00A C004 C007 108.1(3) . . ?
C00A C004 C008 108.2(3) . . ?
C002 C005 C003 127.4(3) . . ?
C002 C005 C009 105.3(3) . . ?
C009 C005 C003 127.3(3) . . ?
C00F C006 C00I 120.6(3) . . ?
C00H C007 C004 109.7(3) . . ?
C00E C008 C004 110.4(3) . . ?
C00B C009 C005 109.0(3) . . ?
C00C C00A C004 110.3(3) . . ?
N001 C00B C00L 127.7(3) . . ?
C009 C00B N001 107.8(3) . . ?
C009 C00B C00L 124.5(3) . . ?
C00A C00C C00K 108.5(3) . . ?
C00G C00C C00A 110.1(3) . . ?
C00G C00C C00K 110.4(3) . . ?
C00H C00D C00E 109.5(3) . . ?
C008 C00E C00D 109.1(3) . . ?
C00K C00E C008 109.8(3) . . ?
C00K C00E C00D 109.4(3) . . ?
C006 C00F C003 121.4(3) . . ?
C00C C00G C00H 108.3(3) . . ?
C00D C00H C007 109.6(3) . . ?
C00D C00H C00G 110.2(3) . . ?
C00G C00H C007 109.8(3) . . ?
C00M C00I C006 118.2(4) . . ?
C00M C00J C003 121.4(4) . . ?
C00E C00K C00C 109.5(3) . . ?
C00I C00M C00J 121.2(4) . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2269834'
loop_
_audit_author_name
_audit_author_address
'Takuya Shimbayashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2023-06-14 deposited with the CCDC.	2023-09-08 downloaded from the CCDC.
;
_audit_creation_date             2023-05-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
shimbayashi.takuya.5z@kyoto-u.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_chemical_melting_point          485-486
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.347(5)
_cell_length_b                   9.721(6)
_cell_length_c                   12.090(7)
_cell_angle_alpha                87.159(17)
_cell_angle_beta                 78.143(15)
_cell_angle_gamma                81.332(16)
_cell_volume                     1062.6(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3397
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[ABSCOR (Rigaku, 1995)]'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8691
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         3.075
_diffrn_ambient_temperature      173.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            Mo
_diffrn_source_type              'Sealed Tube'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3211
_reflns_number_total             4677
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1189
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C8(H8A,H8B,H8C), C23(H23A,H23B,H23C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O22 O 0.42356(12) 0.37497(11) 0.38724(8) 0.0390(3) Uani 1 1 d . . . . .
O7 O 0.54989(13) 0.12872(12) 0.60747(9) 0.0396(3) Uani 1 1 d . . . . .
N16 N 0.65002(13) 0.14363(12) 0.37270(10) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.32929(13) 0.36542(12) 0.62981(10) 0.0261(3) Uani 1 1 d . . . . .
C29 C 0.88462(15) 0.21606(14) -0.00109(12) 0.0234(3) Uani 1 1 d . . . . .
C24 C 0.74427(14) 0.22799(13) 0.06885(11) 0.0208(3) Uani 1 1 d . . . . .
C17 C 0.62034(15) 0.22578(14) 0.28121(11) 0.0236(3) Uani 1 1 d . . . . .
C28 C 0.90269(15) 0.25044(14) -0.11484(12) 0.0239(3) Uani 1 1 d . . . . .
C3 C 0.27266(14) 0.33797(14) 0.81834(11) 0.0215(3) Uani 1 1 d . . . . .
C14 C 0.21865(15) 0.37722(15) 1.02474(12) 0.0242(3) Uani 1 1 d . . . . .
C25 C 0.62268(15) 0.27765(14) 0.01946(11) 0.0236(3) Uani 1 1 d . . . . .
C27 C 0.78136(15) 0.29958(13) -0.16442(11) 0.0231(3) Uani 1 1 d . . . . .
C18 C 0.72900(15) 0.18068(13) 0.18726(11) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.26181(14) 0.28413(13) 0.93556(11) 0.0206(3) Uani 1 1 d . . . . .
C26 C 0.64197(15) 0.31434(14) -0.09404(11) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.36261(15) 0.28082(14) 0.71912(11) 0.0239(3) Uani 1 1 d . . . . .
C10 C 0.28790(15) 0.14222(14) 0.96221(12) 0.0245(3) Uani 1 1 d . . . . .
C21 C 0.50739(16) 0.34363(16) 0.29696(13) 0.0285(3) Uani 1 1 d . . . . .
C4 C 0.18729(16) 0.45895(14) 0.78486(12) 0.0254(3) Uani 1 1 d . . . . .
C20 C 0.77211(16) 0.05027(14) 0.34079(12) 0.0264(3) Uani 1 1 d . . . . .
C12 C 0.22811(15) 0.18789(15) 1.16281(12) 0.0250(3) Uani 1 1 d . . . . .
C19 C 0.82482(16) 0.07161(15) 0.22671(12) 0.0262(3) Uani 1 1 d . . . . .
C5 C 0.22450(16) 0.47317(14) 0.66874(12) 0.0259(3) Uani 1 1 d . . . . .
C13 C 0.20209(15) 0.32959(15) 1.13606(12) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.47874(16) 0.16567(16) 0.70051(12) 0.0298(3) Uani 1 1 d . . . . .
C11 C 0.27214(15) 0.09568(15) 1.07371(12) 0.0260(3) Uani 1 1 d . . . . .
C30 C 0.80174(17) 0.33275(16) -0.28870(12) 0.0321(3) Uani 1 1 d . . . . .
H30A H 0.897242 0.365682 -0.315192 0.048 Uiso 1 1 calc R U . . .
H30B H 0.722235 0.405406 -0.302576 0.048 Uiso 1 1 calc R U . . .
H30C H 0.799043 0.248850 -0.329500 0.048 Uiso 1 1 calc R U . . .
C8 C 0.16599(18) 0.58059(16) 0.59057(13) 0.0369(4) Uani 1 1 d . . . . .
H8A H 0.247949 0.606588 0.532736 0.055 Uiso 1 1 calc R U . . .
H8B H 0.115348 0.662968 0.633479 0.055 Uiso 1 1 calc R U . . .
H8C H 0.096227 0.542787 0.554147 0.055 Uiso 1 1 calc R U . . .
C23 C 0.82916(18) -0.05304(16) 0.42259(13) 0.0369(4) Uani 1 1 d . . . . .
H23A H 0.868475 -0.004759 0.476471 0.055 Uiso 1 1 calc R U . . .
H23B H 0.907835 -0.121039 0.381499 0.055 Uiso 1 1 calc R U . . .
H23C H 0.748614 -0.101163 0.463504 0.055 Uiso 1 1 calc R U . . .
C15 C 0.20804(18) 0.13630(17) 1.28340(12) 0.0359(4) Uani 1 1 d . . . . .
H15A H 0.298234 0.076512 1.294917 0.054 Uiso 1 1 calc R U . . .
H15B H 0.124892 0.082935 1.300105 0.054 Uiso 1 1 calc R U . . .
H15C H 0.187883 0.215778 1.333876 0.054 Uiso 1 1 calc R U . . .
H16 H 0.6016(17) 0.1481(16) 0.4422(14) 0.035(5) Uiso 1 1 d . . . . .
H1 H 0.3711(17) 0.3560(16) 0.5561(14) 0.032(4) Uiso 1 1 d . . . . .
H21 H 0.4991(15) 0.4060(14) 0.2268(12) 0.024(4) Uiso 1 1 d . . . . .
H6 H 0.5034(16) 0.1120(15) 0.7703(13) 0.033(4) Uiso 1 1 d . . . . .
H4 H 0.1106(17) 0.5233(15) 0.8330(12) 0.030(4) Uiso 1 1 d . . . . .
H19 H 0.9124(17) 0.0128(15) 0.1815(12) 0.028(4) Uiso 1 1 d . . . . .
H25 H 0.5240(16) 0.2839(14) 0.0640(12) 0.024(4) Uiso 1 1 d . . . . .
H29 H 0.9705(17) 0.1816(15) 0.0310(12) 0.032(4) Uiso 1 1 d . . . . .
H28 H 1.0002(16) 0.2429(14) -0.1659(12) 0.028(4) Uiso 1 1 d . . . . .
H26 H 0.5527(16) 0.3520(14) -0.1261(11) 0.025(4) Uiso 1 1 d . . . . .
H10 H 0.3154(17) 0.0756(15) 0.9011(12) 0.032(4) Uiso 1 1 d . . . . .
H14 H 0.1927(16) 0.4739(15) 1.0092(11) 0.026(4) Uiso 1 1 d . . . . .
H11 H 0.2925(15) -0.0045(15) 1.0883(11) 0.025(4) Uiso 1 1 d . . . . .
H13 H 0.1716(15) 0.3957(15) 1.1971(12) 0.026(4) 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
O22 C21 1.2278(18) . ?
O7 C6 1.2236(18) . ?
N16 C17 1.3819(18) . ?
N16 C20 1.3476(19) . ?
N16 H16 0.869(17) . ?
N1 C2 1.3828(17) . ?
N1 C5 1.3521(19) . ?
N1 H1 0.900(16) . ?
C29 C24 1.3991(19) . ?
C29 C28 1.381(2) . ?
C29 H29 0.970(15) . ?
C24 C25 1.4022(19) . ?
C24 C18 1.467(2) . ?
C17 C18 1.3982(19) . ?
C17 C21 1.427(2) . ?
C28 C27 1.401(2) . ?
C28 H28 0.985(14) . ?
C3 C9 1.475(2) . ?
C3 C2 1.402(2) . ?
C3 C4 1.4093(19) . ?
C14 C9 1.3972(19) . ?
C14 C13 1.387(2) . ?
C14 H14 0.954(14) . ?
C25 C26 1.383(2) . ?
C25 H25 0.963(14) . ?
C27 C26 1.394(2) . ?
C27 C30 1.500(2) . ?
C18 C19 1.4118(19) . ?
C9 C10 1.398(2) . ?
C26 H26 1.004(14) . ?
C2 C6 1.428(2) . ?
C10 C11 1.386(2) . ?
C10 H10 0.975(16) . ?
C21 H21 1.027(13) . ?
C4 C5 1.380(2) . ?
C4 H4 0.987(15) . ?
C20 C19 1.382(2) . ?
C20 C23 1.4926(19) . ?
C12 C13 1.396(2) . ?
C12 C11 1.391(2) . ?
C12 C15 1.502(2) . ?
C19 H19 1.001(15) . ?
C5 C8 1.4916(19) . ?
C13 H13 0.972(15) . ?
C6 H6 1.018(14) . ?
C11 H11 0.978(14) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C17 N16 H16 128.1(10) . . ?
C20 N16 C17 110.17(12) . . ?
C20 N16 H16 121.8(10) . . ?
C2 N1 H1 127.5(10) . . ?
C5 N1 C2 109.95(12) . . ?
C5 N1 H1 122.5(10) . . ?
C24 C29 H29 119.1(9) . . ?
C28 C29 C24 121.26(12) . . ?
C28 C29 H29 119.6(9) . . ?
C29 C24 C25 117.54(13) . . ?
C29 C24 C18 119.52(12) . . ?
C25 C24 C18 122.83(13) . . ?
N16 C17 C18 107.41(12) . . ?
N16 C17 C21 120.32(13) . . ?
C18 C17 C21 131.71(13) . . ?
C29 C28 C27 121.30(13) . . ?
C29 C28 H28 122.9(8) . . ?
C27 C28 H28 115.8(8) . . ?
C2 C3 C9 128.61(12) . . ?
C2 C3 C4 106.31(12) . . ?
C4 C3 C9 125.06(13) . . ?
C9 C14 H14 119.6(8) . . ?
C13 C14 C9 120.77(14) . . ?
C13 C14 H14 119.4(8) . . ?
C24 C25 H25 120.1(8) . . ?
C26 C25 C24 120.83(13) . . ?
C26 C25 H25 119.0(8) . . ?
C28 C27 C30 120.90(13) . . ?
C26 C27 C28 117.32(13) . . ?
C26 C27 C30 121.78(12) . . ?
C17 C18 C24 129.46(12) . . ?
C17 C18 C19 106.21(12) . . ?
C19 C18 C24 124.29(13) . . ?
C14 C9 C3 119.31(13) . . ?
C14 C9 C10 117.91(13) . . ?
C10 C9 C3 122.74(13) . . ?
C25 C26 C27 121.73(12) . . ?
C25 C26 H26 118.7(8) . . ?
C27 C26 H26 119.6(8) . . ?
N1 C2 C3 107.34(12) . . ?
N1 C2 C6 120.56(13) . . ?
C3 C2 C6 131.93(13) . . ?
C9 C10 H10 119.0(8) . . ?
C11 C10 C9 120.90(13) . . ?
C11 C10 H10 120.1(8) . . ?
O22 C21 C17 124.70(14) . . ?
O22 C21 H21 119.3(8) . . ?
C17 C21 H21 116.0(8) . . ?
C3 C4 H4 127.9(8) . . ?
C5 C4 C3 108.43(13) . . ?
C5 C4 H4 123.6(8) . . ?
N16 C20 C19 107.82(12) . . ?
N16 C20 C23 121.70(13) . . ?
C19 C20 C23 130.48(13) . . ?
C13 C12 C15 121.33(14) . . ?
C11 C12 C13 117.64(13) . . ?
C11 C12 C15 121.03(14) . . ?
C18 C19 H19 127.8(8) . . ?
C20 C19 C18 108.38(13) . . ?
C20 C19 H19 123.7(8) . . ?
N1 C5 C4 107.96(12) . . ?
N1 C5 C8 121.60(13) . . ?
C4 C5 C8 130.43(14) . . ?
C14 C13 C12 121.38(13) . . ?
C14 C13 H13 119.7(8) . . ?
C12 C13 H13 118.9(8) . . ?
O7 C6 C2 124.54(14) . . ?
O7 C6 H6 118.6(9) . . ?
C2 C6 H6 116.9(9) . . ?
C10 C11 C12 121.39(14) . . ?
C10 C11 H11 118.0(8) . . ?
C12 C11 H11 120.6(8) . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N16 C17 C18 C24 176.63(13) . . . . ?
N16 C17 C18 C19 -1.12(15) . . . . ?
N16 C17 C21 O22 -5.4(2) . . . . ?
N16 C20 C19 C18 -1.20(17) . . . . ?
N1 C2 C6 O7 -4.2(2) . . . . ?
C29 C24 C25 C26 -0.5(2) . . . . ?
C29 C24 C18 C17 152.80(14) . . . . ?
C29 C24 C18 C19 -29.8(2) . . . . ?
C29 C28 C27 C26 0.9(2) . . . . ?
C29 C28 C27 C30 -178.23(13) . . . . ?
C24 C29 C28 C27 0.5(2) . . . . ?
C24 C25 C26 C27 2.0(2) . . . . ?
C24 C18 C19 C20 -176.47(13) . . . . ?
C17 N16 C20 C19 0.50(17) . . . . ?
C17 N16 C20 C23 -179.42(13) . . . . ?
C17 C18 C19 C20 1.43(16) . . . . ?
C28 C29 C24 C25 -0.7(2) . . . . ?
C28 C29 C24 C18 175.49(12) . . . . ?
C28 C27 C26 C25 -2.2(2) . . . . ?
C3 C9 C10 C11 -178.02(13) . . . . ?
C3 C2 C6 O7 -178.90(16) . . . . ?
C3 C4 C5 N1 0.07(17) . . . . ?
C3 C4 C5 C8 178.78(15) . . . . ?
C14 C9 C10 C11 -0.3(2) . . . . ?
C25 C24 C18 C17 -31.2(2) . . . . ?
C25 C24 C18 C19 146.17(14) . . . . ?
C18 C24 C25 C26 -176.60(13) . . . . ?
C18 C17 C21 O22 -175.69(16) . . . . ?
C9 C3 C2 N1 177.48(13) . . . . ?
C9 C3 C2 C6 -7.3(3) . . . . ?
C9 C3 C4 C5 -177.86(13) . . . . ?
C9 C14 C13 C12 0.1(2) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C2 N1 C5 C4 -0.51(17) . . . . ?
C2 N1 C5 C8 -179.36(13) . . . . ?
C2 C3 C9 C14 152.74(14) . . . . ?
C2 C3 C9 C10 -29.6(2) . . . . ?
C2 C3 C4 C5 0.39(16) . . . . ?
C21 C17 C18 C24 -12.1(3) . . . . ?
C21 C17 C18 C19 170.11(15) . . . . ?
C4 C3 C9 C14 -29.4(2) . . . . ?
C4 C3 C9 C10 148.23(14) . . . . ?
C4 C3 C2 N1 -0.69(15) . . . . ?
C4 C3 C2 C6 174.48(16) . . . . ?
C20 N16 C17 C18 0.41(16) . . . . ?
C20 N16 C17 C21 -172.02(13) . . . . ?
C5 N1 C2 C3 0.76(16) . . . . ?
C5 N1 C2 C6 -175.07(14) . . . . ?
C13 C14 C9 C3 177.61(13) . . . . ?
C13 C14 C9 C10 -0.1(2) . . . . ?
C13 C12 C11 C10 -0.8(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C30 C27 C26 C25 176.96(13) . . . . ?
C23 C20 C19 C18 178.70(15) . . . . ?
C15 C12 C13 C14 -179.11(14) . . . . ?
C15 C12 C11 C10 178.62(14) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2269833'
loop_
_audit_author_name
_audit_author_address
'Takuya Shimbayashi'
;Kyoto University
Japan
;
_audit_update_record             
;
2023-06-14 deposited with the CCDC.	2023-09-08 downloaded from the CCDC.
;
_audit_creation_date             2021-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 N2 O'
_chemical_formula_sum            'C18 H24 N2 O'
_chemical_formula_weight         284.39
_chemical_melting_point          385-386
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.6949(16)
_cell_length_b                   23.640(7)
_cell_length_c                   11.681(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.821(4)
_cell_angle_gamma                90
_cell_volume                     1561.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4093
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.4
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12352
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_temperature      173.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Sealed Tube'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2817
_reflns_number_total             3507
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.2645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
2.b Idealised Me refined as rotating group:
 C00F(H00F,H00G,H00H), C00G(H00I,H00J,H00K), C00I(H00L,H00M,H00N), C00J(H00O,
 H00P,H00Q), C00K(H00R,H00S,H00T), C00L(H00U,H00V,H00W)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.5088(2) 0.30296(4) 0.82486(8) 0.0369(3) Uani 1 1 d . . . . .
N002 N 0.37922(18) 0.34461(4) 0.57201(9) 0.0224(2) Uani 1 1 d . . . . .
N3 N 1.0059(2) 0.59721(5) 0.93282(11) 0.0361(3) Uani 1 1 d . . . . .
C004 C 0.6932(2) 0.46762(5) 0.71619(11) 0.0240(3) Uani 1 1 d . . . . .
C005 C 0.5802(2) 0.42335(5) 0.63980(11) 0.0229(3) Uani 1 1 d . . . . .
C006 C 0.4717(2) 0.37347(5) 0.67301(11) 0.0221(3) Uani 1 1 d . . . . .
C007 C 0.5334(2) 0.35061(6) 0.78645(11) 0.0262(3) Uani 1 1 d . . . . .
H007 H 0.605783 0.376906 0.841192 0.031 Uiso 1 1 calc R . . . .
C008 C 0.9077(2) 0.55416(5) 0.86306(12) 0.0261(3) Uani 1 1 d . . . . .
C009 C 0.4451(2) 0.37408(6) 0.47990(11) 0.0263(3) Uani 1 1 d . . . . .
C00A C 0.7050(2) 0.52544(6) 0.88882(12) 0.0273(3) Uani 1 1 d . . . . .
H00A H 0.639060 0.534408 0.957570 0.033 Uiso 1 1 calc R . . . .
C00B C 0.5996(2) 0.48436(6) 0.81603(11) 0.0261(3) Uani 1 1 d . . . . .
H00B H 0.458639 0.466894 0.834494 0.031 Uiso 1 1 calc R . . . .
C00C C 0.5653(2) 0.42230(6) 0.51962(11) 0.0281(3) Uani 1 1 d . . . . .
H00C H 0.627621 0.450135 0.472917 0.034 Uiso 1 1 calc R . . . .
C00D C 0.8975(2) 0.49564(6) 0.69136(12) 0.0281(3) Uani 1 1 d . . . . .
H00D H 0.966453 0.485388 0.624132 0.034 Uiso 1 1 calc R . . . .
C00E C 1.0021(2) 0.53787(6) 0.76199(12) 0.0282(3) Uani 1 1 d . . . . .
H00E H 1.139990 0.556178 0.741933 0.034 Uiso 1 1 calc R . . . .
C00F C 0.3561(3) 0.24100(6) 0.59236(13) 0.0311(3) Uani 1 1 d . . . . .
H00F H 0.446941 0.234327 0.527464 0.047 Uiso 1 1 calc GR . . . .
H00G H 0.249560 0.209001 0.599780 0.047 Uiso 1 1 calc GR . . . .
H00H H 0.464719 0.244943 0.663526 0.047 Uiso 1 1 calc GR . . . .
C00G C 1.1970(2) 0.63071(6) 0.89914(13) 0.0334(3) Uani 1 1 d . . . . .
H00I H 1.331982 0.606126 0.889705 0.050 Uiso 1 1 calc GR . . . .
H00J H 1.244039 0.659023 0.958752 0.050 Uiso 1 1 calc GR . . . .
H00K H 1.145366 0.649794 0.825999 0.050 Uiso 1 1 calc GR . . . .
C00H C 0.2116(2) 0.29501(5) 0.57106(12) 0.0259(3) Uani 1 1 d . . . . .
C00I C 0.9107(3) 0.60994(6) 1.03921(12) 0.0303(3) Uani 1 1 d . . . . .
H00L H 0.742149 0.618928 1.022576 0.045 Uiso 1 1 calc GR . . . .
H00M H 0.994748 0.642446 1.076602 0.045 Uiso 1 1 calc GR . . . .
H00N H 0.930784 0.577084 1.090596 0.045 Uiso 1 1 calc GR . . . .
C00J C 0.4133(3) 0.35660(7) 0.35578(12) 0.0381(4) Uani 1 1 d . . . . .
H00O H 0.464803 0.317298 0.349301 0.057 Uiso 1 1 calc GR . . . .
H00P H 0.508149 0.381202 0.311764 0.057 Uiso 1 1 calc GR . . . .
H00Q H 0.246064 0.359870 0.325045 0.057 Uiso 1 1 calc GR . . . .
C00K C 0.0525(3) 0.29010(7) 0.45618(14) 0.0404(4) Uani 1 1 d . . . . .
H00R H -0.017978 0.327042 0.435241 0.061 Uiso 1 1 calc GR . . . .
H00S H -0.073151 0.262522 0.463768 0.061 Uiso 1 1 calc GR . . . .
H00T H 0.147002 0.277601 0.396013 0.061 Uiso 1 1 calc GR . . . .
C00L C 0.0467(3) 0.30515(6) 0.66361(14) 0.0358(4) Uani 1 1 d . . . . .
H00U H 0.140021 0.306749 0.739633 0.054 Uiso 1 1 calc GR . . . .
H00V H -0.067984 0.274173 0.662133 0.054 Uiso 1 1 calc GR . . . .
H00W H -0.037429 0.341027 0.648252 0.054 Uiso 1 1 calc GR . . . .


_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
O001 C007 1.2267(16) . ?
N002 C006 1.4096(16) . ?
N002 C009 1.3709(16) . ?
N002 C00H 1.5114(17) . ?
N3 C008 1.3802(17) . ?
N3 C00G 1.4380(18) . ?
N3 C00I 1.4453(18) . ?
C004 C005 1.4728(18) . ?
C004 C00B 1.3959(18) . ?
C004 C00D 1.3990(19) . ?
C005 C006 1.4070(18) . ?
C005 C00C 1.3965(18) . ?
C006 C007 1.4356(18) . ?
C008 C00A 1.4022(19) . ?
C008 C00E 1.4080(19) . ?
C009 C00C 1.3814(19) . ?
C009 C00J 1.4978(19) . ?
C00A C00B 1.3802(18) . ?
C00D C00E 1.3839(19) . ?
C00F C00H 1.5232(18) . ?
C00H C00K 1.532(2) . ?
C00H C00L 1.5328(19) . ?

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
C006 N002 C00H 123.68(10) . . ?
C009 N002 C006 107.52(11) . . ?
C009 N002 C00H 128.31(11) . . ?
C008 N3 C00G 120.77(12) . . ?
C008 N3 C00I 119.60(12) . . ?
C00G N3 C00I 119.60(12) . . ?
C00B C004 C005 121.66(12) . . ?
C00B C004 C00D 116.66(12) . . ?
C00D C004 C005 121.68(12) . . ?
C006 C005 C004 127.09(12) . . ?
C00C C005 C004 126.27(12) . . ?
C00C C005 C006 106.62(11) . . ?
N002 C006 C007 128.06(12) . . ?
C005 C006 N002 107.91(11) . . ?
C005 C006 C007 120.17(12) . . ?
O001 C007 C006 131.09(13) . . ?
N3 C008 C00A 121.12(12) . . ?
N3 C008 C00E 121.89(12) . . ?
C00A C008 C00E 116.98(12) . . ?
N002 C009 C00C 109.06(11) . . ?
N002 C009 C00J 127.35(12) . . ?
C00C C009 C00J 123.43(12) . . ?
C00B C00A C008 121.15(12) . . ?
C00A C00B C004 122.20(12) . . ?
C009 C00C C005 108.71(12) . . ?
C00E C00D C004 121.84(12) . . ?
C00D C00E C008 121.13(12) . . ?
N002 C00H C00F 108.69(11) . . ?
N002 C00H C00K 111.87(11) . . ?
N002 C00H C00L 108.22(10) . . ?
C00F C00H C00K 109.36(12) . . ?
C00F C00H C00L 112.35(12) . . ?
C00K C00H C00L 106.37(12) . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
