# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Cocrystal1
_database_code_depnum_ccdc_archive 'CCDC 1840880'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N2'
_chemical_formula_weight         259.32

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9929(2)
_cell_length_b                   9.6745(3)
_cell_length_c                   10.9094(3)
_cell_angle_alpha                97.057(2)
_cell_angle_beta                 97.633(2)
_cell_angle_gamma                96.111(2)
_cell_volume                     720.29(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2600
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      67.44

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             274
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10553
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         67.44
_reflns_number_total             2600
_reflns_number_gt                2260
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1203P)²+0.0706P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   constr
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2600
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.45854(15) 0.46877(12) 0.43852(11) 0.0361(3) Uani 1 1 d . . .
C3 C 0.38081(17) 0.32465(13) 0.41523(12) 0.0393(3) Uani 1 1 d . . .
C6 C 0.45204(16) 0.54892(13) 0.33829(12) 0.0392(3) Uani 1 1 d . . .
C13 C 0.07150(17) 0.64219(14) 0.50040(13) 0.0432(3) Uani 1 1 d . . .
C4 C 0.38880(17) 0.24617(13) 0.51902(13) 0.0432(3) Uani 1 1 d . . .
H4 H 0.3381 0.1518 0.5054 0.052 Uiso 1 1 calc R . .
C5 C 0.46768(18) 0.30537(13) 0.63563(13) 0.0426(3) Uani 1 1 d . . .
H5 H 0.4703 0.2511 0.7004 0.051 Uiso 1 1 calc R . .
C7 C 0.37123(18) 0.48388(14) 0.21869(13) 0.0449(4) Uani 1 1 d . . .
H7 H 0.3660 0.5372 0.1533 0.054 Uiso 1 1 calc R . .
C2 C 0.30325(19) 0.26499(13) 0.29386(13) 0.0458(4) Uani 1 1 d . . .
H2 H 0.2531 0.1705 0.2790 0.055 Uiso 1 1 calc R . .
C1 C 0.29803(18) 0.34202(14) 0.19343(13) 0.0474(4) Uani 1 1 d . . .
C14 C -0.02289(18) 0.55613(15) 0.38737(13) 0.0457(4) Uani 1 1 d . . .
H15 H -0.0369 0.5949 0.3133 0.055 Uiso 1 1 calc R . .
C15 C -0.09116(18) 0.42133(15) 0.38638(13) 0.0456(4) Uani 1 1 d . . .
H14 H -0.1519 0.3680 0.3119 0.055 Uiso 1 1 calc R . .
C16 C 0.14043(19) 0.78092(15) 0.50110(14) 0.0494(4) Uani 1 1 d . . .
N1 N 0.3106(3) 0.94388(17) 0.69847(16) 0.0840(5) Uani 1 1 d . . .
N2 N 0.1112(3) 0.89906(17) 0.30220(16) 0.0851(5) Uani 1 1 d . . .
C9 C 0.2167(2) 0.26763(17) 0.06183(14) 0.0605(4) Uani 1 1 d . . .
C18 C 0.1231(2) 0.84556(15) 0.39028(16) 0.0591(4) Uani 1 1 d . . .
C17 C 0.2345(2) 0.86981(15) 0.61158(16) 0.0581(4) Uani 1 1 d . . .
C12 C 0.0025(3) 0.2120(3) 0.05820(18) 0.0979(8) Uani 1 1 d . . .
H12A H -0.0091 0.1513 0.1208 0.147 Uiso 1 1 calc R . .
H12C H -0.0476 0.1605 -0.0227 0.147 Uiso 1 1 calc R . .
H12B H -0.0702 0.2894 0.0742 0.147 Uiso 1 1 calc R . .
C10 C 0.2253(4) 0.3652(2) -0.03743(17) 0.0964(8) Uani 1 1 d . . .
H10A H 0.1584 0.4443 -0.0159 0.145 Uiso 1 1 calc R . .
H10B H 0.1643 0.3154 -0.1170 0.145 Uiso 1 1 calc R . .
H10C H 0.3586 0.3972 -0.0420 0.145 Uiso 1 1 calc R . .
C11 C 0.3301(4) 0.1461(3) 0.0299(2) 0.1176(10) Uani 1 1 d . . .
H11A H 0.4614 0.1818 0.0238 0.176 Uiso 1 1 calc R . .
H11B H 0.2701 0.0929 -0.0484 0.176 Uiso 1 1 calc R . .
H11C H 0.3305 0.0867 0.0943 0.176 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
C8 C6 1.4148(18) . ?
C8 C3 1.4209(18) . ?
C8 C8 1.421(2) 2_666 ?
C3 C2 1.3912(19) . ?
C3 C4 1.4370(18) . ?
C6 C7 1.3944(19) . ?
C6 C5 1.4400(17) 2_666 ?
C13 C16 1.376(2) . ?
C13 C14 1.437(2) . ?
C13 C15 1.443(2) 2_566 ?
C4 C5 1.3483(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.4401(17) 2_666 ?
C5 H5 0.9300 . ?
C7 C1 1.3934(19) . ?
C7 H7 0.9300 . ?
C2 C1 1.397(2) . ?
C2 H2 0.9300 . ?
C1 C9 1.5313(19) . ?
C14 C15 1.338(2) . ?
C14 H15 0.9300 . ?
C15 C13 1.443(2) 2_566 ?
C15 H14 0.9300 . ?
C16 C18 1.425(2) . ?
C16 C17 1.428(2) . ?
N1 C17 1.146(2) . ?
N2 C18 1.144(2) . ?
C9 C11 1.518(3) . ?
C9 C10 1.524(2) . ?
C9 C12 1.530(3) . ?
C12 H12A 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12B 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C6 C8 C3 119.31(12) . . ?
C6 C8 C8 120.60(13) . 2_666 ?
C3 C8 C8 120.09(14) . 2_666 ?
C2 C3 C8 119.17(12) . . ?
C2 C3 C4 122.82(11) . . ?
C8 C3 C4 118.01(12) . . ?
C7 C6 C8 119.05(11) . . ?
C7 C6 C5 122.76(12) . 2_666 ?
C8 C6 C5 118.19(12) . 2_666 ?
C16 C13 C14 121.21(13) . . ?
C16 C13 C15 120.91(13) . 2_566 ?
C14 C13 C15 117.88(12) . 2_566 ?
C5 C4 C3 121.91(11) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 121.21(12) . 2_666 ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 2_666 . ?
C1 C7 C6 122.53(12) . . ?
C1 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C3 C2 C1 122.32(12) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C7 C1 C2 117.60(12) . . ?
C7 C1 C9 123.17(13) . . ?
C2 C1 C9 119.21(12) . . ?
C15 C14 C13 121.42(13) . . ?
C15 C14 H15 119.3 . . ?
C13 C14 H15 119.3 . . ?
C14 C15 C13 120.70(14) . 2_566 ?
C14 C15 H14 119.6 . . ?
C13 C15 H14 119.6 2_566 . ?
C13 C16 C18 121.81(14) . . ?
C13 C16 C17 122.83(13) . . ?
C18 C16 C17 115.36(12) . . ?
C11 C9 C10 109.09(18) . . ?
C11 C9 C12 109.56(19) . . ?
C10 C9 C12 107.03(16) . . ?
C11 C9 C1 109.37(15) . . ?
C10 C9 C1 112.77(13) . . ?
C12 C9 C1 108.97(13) . . ?
N2 C18 C16 178.96(17) . . ?
N1 C17 C16 178.26(16) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.44
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.128
####################################################################### 
# 
# 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_Cocrystal3
_database_code_depnum_ccdc_archive 'CCDC 1840882'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT770_Cocrystal3          
;
PROBLEM: Suspect C-H Bond in CIF:  C24A     --H22C      .       1.52 Ang.
RESPONSE: Disordered tert-butyl group
;
_vrf_PLAT029_Cocrystal3          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.959 Why?
RESPONSE: Small size of crystal
;
_vrf_PLAT430_Cocrystal3          
;
PROBLEM: Short Inter D...A Contact  O4       ..O4               2.81 Ang.
RESPONSE: Intermolecular O...O contact
;
# Added during the CSD deposition process: Wednesday 02 May 2018 05:05 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H30 N2 O4'
_chemical_formula_weight         482.56

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9689(2)
_cell_length_b                   10.7206(3)
_cell_length_c                   18.5310(4)
_cell_angle_alpha                97.772(2)
_cell_angle_beta                 100.438(2)
_cell_angle_gamma                107.389(3)
_cell_volume                     1272.60(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5247
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      78.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD plate'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18918
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         78.53
_reflns_number_total             5247
_reflns_number_gt                4056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0020P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5247
_refine_ls_number_parameters     391
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.1524
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      1.127
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.6794(4) 0.5192(3) 0.47256(14) 0.0968(9) Uani 1 1 d . . .
C15 C 0.8594(3) 0.4007(2) 0.25755(13) 0.0404(5) Uani 1 1 d . . .
N2 N 0.6148(4) 0.5818(4) 0.42931(16) 0.0740(8) Uani 1 1 d . . .
C16 C 0.8882(3) 0.5068(2) 0.21790(13) 0.0408(5) Uani 1 1 d . . .
C6 C 0.9872(4) 0.6407(2) 0.25718(14) 0.0428(5) Uani 1 1 d . . .
C3 C 0.9311(3) 0.4271(2) 0.33613(13) 0.0411(5) Uani 1 1 d . . .
C4 C 1.0342(4) 0.5637(3) 0.37435(14) 0.0456(6) Uani 1 1 d . . .
H4A H 1.0846 0.5828 0.4260 0.055 Uiso 1 1 calc R . .
C1 C 0.7934(4) 0.1897(3) 0.33693(15) 0.0480(6) Uani 1 1 d . . .
C13 C 0.7583(4) 0.2665(3) 0.21834(14) 0.0468(6) Uani 1 1 d . . .
C2 C 0.8968(4) 0.3213(3) 0.37399(14) 0.0462(6) Uani 1 1 d . . .
H2 H 0.9449 0.3394 0.4258 0.055 Uiso 1 1 calc R . .
C5 C 1.0592(4) 0.6645(3) 0.33690(14) 0.0467(6) Uani 1 1 d . . .
H5 H 1.1248 0.7518 0.3635 0.056 Uiso 1 1 calc R . .
C10 C 0.8172(4) 0.4805(3) 0.13917(14) 0.0474(6) Uani 1 1 d . . .
C7 C 1.0123(4) 0.7429(3) 0.21675(15) 0.0492(6) Uani 1 1 d . . .
H7 H 1.0773 0.8307 0.2427 0.059 Uiso 1 1 calc R . .
O3 O 0.6344(5) 0.6993(3) 0.44484(17) 0.1112(10) Uani 1 1 d . . .
O2 O 0.4680(6) 0.7063(5) 0.1819(2) 0.1275(14) Uani 1 1 d . . .
C14 C 0.7279(4) 0.1651(3) 0.25913(15) 0.0516(6) Uani 1 1 d . . .
H14 H 0.6613 0.0774 0.2334 0.062 Uiso 1 1 calc R . .
C8 C 0.9439(4) 0.7187(3) 0.13920(15) 0.0513(6) Uani 1 1 d . . .
N1 N 0.3905(6) 0.5847(6) 0.1649(2) 0.1014(13) Uani 1 1 d . . .
C9 C 0.8474(4) 0.5865(3) 0.10171(15) 0.0542(7) Uani 1 1 d . . .
H9 H 0.8015 0.5682 0.0498 0.065 Uiso 1 1 calc R . .
C12 C 0.6890(5) 0.2429(3) 0.13844(15) 0.0578(7) Uani 1 1 d . . .
H12 H 0.6231 0.1557 0.1118 0.069 Uiso 1 1 calc R . .
C17 C 0.7541(5) 0.0742(3) 0.37890(17) 0.0576(7) Uani 1 1 d . . .
C29 C 0.5037(4) 0.5084(3) 0.35288(17) 0.0592(7) Uani 1 1 d . . .
C30 C 0.4945(4) 0.5798(4) 0.29710(18) 0.0631(8) Uani 1 1 d . . .
H30 H 0.5529 0.6723 0.3071 0.076 Uiso 1 1 calc R . .
C11 C 0.7168(4) 0.3436(3) 0.10086(15) 0.0578(7) Uani 1 1 d . . .
H11 H 0.6702 0.3241 0.0490 0.069 Uiso 1 1 calc R . .
C21 C 0.9761(5) 0.8333(3) 0.09662(17) 0.0611(7) Uani 1 1 d . . .
C25 C 0.3956(5) 0.5091(4) 0.22606(19) 0.0720(9) Uani 1 1 d . . .
C28 C 0.4165(5) 0.3726(4) 0.3406(2) 0.0738(9) Uani 1 1 d . . .
H28 H 0.4260 0.3271 0.3797 0.089 Uiso 1 1 calc R . .
O1 O 0.3103(6) 0.5215(5) 0.10155(18) 0.1519(17) Uani 1 1 d . . .
C26 C 0.3047(5) 0.3722(5) 0.2107(2) 0.0890(13) Uani 1 1 d . . .
H26 H 0.2379 0.3260 0.1620 0.107 Uiso 1 1 calc R . .
C27 C 0.3149(6) 0.3054(4) 0.2690(3) 0.0894(12) Uani 1 1 d . . .
H29 H 0.2519 0.2133 0.2596 0.107 Uiso 1 1 calc R . .
C20 C 0.7946(8) 0.1223(4) 0.4636(2) 0.1012(14) Uani 1 1 d . . .
H20A H 0.7103 0.1758 0.4737 0.152 Uiso 1 1 calc R . .
H20B H 0.9378 0.1747 0.4830 0.152 Uiso 1 1 calc R . .
H20C H 0.7611 0.0466 0.4871 0.152 Uiso 1 1 calc R . .
C19 C 0.5300(6) -0.0175(4) 0.3529(3) 0.1065(15) Uani 1 1 d . . .
H19A H 0.5017 -0.0570 0.3008 0.160 Uiso 1 1 calc R . .
H19B H 0.4399 0.0332 0.3600 0.160 Uiso 1 1 calc R . .
H19C H 0.5072 -0.0865 0.3816 0.160 Uiso 1 1 calc R . .
C18 C 0.8955(8) -0.0047(5) 0.3646(3) 0.1140(17) Uani 1 1 d . . .
H18A H 0.8742 -0.0757 0.3919 0.171 Uiso 1 1 calc R . .
H18B H 1.0368 0.0531 0.3808 0.171 Uiso 1 1 calc R . .
H18C H 0.8651 -0.0415 0.3120 0.171 Uiso 1 1 calc R . .
C24A C 1.2116(14) 0.9087(14) 0.1097(8) 0.112(4) Uani 0.50 1 d PD . .
C23 C 0.864(3) 0.9262(14) 0.1229(10) 0.120(4) Uani 0.50 1 d PD . .
C22 C 0.899(2) 0.7829(11) 0.0086(5) 0.108(3) Uani 0.50 1 d PD . .
C23A C 0.7599(15) 0.8222(13) 0.0511(8) 0.102(3) Uani 0.50 1 d PD . .
C24 C 1.076(2) 0.9711(8) 0.1500(5) 0.090(3) Uani 0.50 1 d PD . .
C22A C 1.108(2) 0.8098(13) 0.0426(7) 0.100(3) Uani 0.50 1 d PD . .
H23A H 0.709(4) 0.861(5) 0.0970(19) 0.16(3) Uiso 1 1 d D . .
H24A H 1.221(6) 0.962(6) 0.161(2) 0.19(3) Uiso 1 1 d D . .
H22A H 1.007(6) 0.759(8) 0.006(4) 0.36(8) Uiso 1 1 d D . .
H23B H 0.960(4) 0.975(8) 0.166(3) 0.27(6) Uiso 1 1 d D . .
H22B H 0.756(4) 0.760(6) 0.011(3) 0.25(5) Uiso 1 1 d D . .
H24B H 1.248(5) 0.836(5) 0.079(2) 0.16(3) Uiso 1 1 d D . .
H22C H 1.126(13) 0.883(5) 0.026(5) 0.25(4) Uiso 1 1 d D . .
H23C H 0.784(12) 0.889(5) 0.033(5) 0.25(4) Uiso 1 1 d D . .
H24C H 1.078(12) 1.019(6) 0.122(3) 0.22(3) Uiso 1 1 d 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
O4 N2 1.221(4) . ?
C15 C3 1.411(3) . ?
C15 C16 1.421(3) . ?
C15 C13 1.421(3) . ?
N2 O3 1.213(4) . ?
N2 C29 1.470(4) . ?
C16 C10 1.413(3) . ?
C16 C6 1.417(3) . ?
C6 C7 1.396(3) . ?
C6 C5 1.432(3) . ?
C3 C2 1.397(3) . ?
C3 C4 1.437(3) . ?
C4 C5 1.347(3) . ?
C4 H4A 0.9300 . ?
C1 C2 1.389(4) . ?
C1 C14 1.394(4) . ?
C1 C17 1.532(4) . ?
C13 C14 1.393(4) . ?
C13 C12 1.434(4) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C10 C9 1.392(4) . ?
C10 C11 1.440(4) . ?
C7 C8 1.392(4) . ?
C7 H7 0.9300 . ?
O2 N1 1.224(5) . ?
C14 H14 0.9300 . ?
C8 C9 1.393(4) . ?
C8 C21 1.531(4) . ?
N1 O1 1.213(5) . ?
N1 C25 1.480(5) . ?
C9 H9 0.9300 . ?
C12 C11 1.347(4) . ?
C12 H12 0.9300 . ?
C17 C18 1.513(5) . ?
C17 C19 1.523(5) . ?
C17 C20 1.530(5) . ?
C29 C28 1.369(5) . ?
C29 C30 1.370(4) . ?
C30 C25 1.368(5) . ?
C30 H30 0.9300 . ?
C11 H11 0.9300 . ?
C21 C23 1.520(10) . ?
C21 C22A 1.523(9) . ?
C21 C24 1.545(9) . ?
C21 C23A 1.550(9) . ?
C21 C24A 1.554(9) . ?
C21 C22 1.584(9) . ?
C25 C26 1.379(6) . ?
C28 C27 1.370(5) . ?
C28 H28 0.9300 . ?
C26 C27 1.377(6) . ?
C26 H26 0.9300 . ?
C27 H29 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C24A C22A 1.43(2) . ?
C24A C24 1.55(2) . ?
C24A H24A 1.02(2) . ?
C24A H24B 1.02(2) . ?
C24A H22C 1.52(8) . ?
C23 C24 1.38(2) . ?
C23 C23A 1.52(2) . ?
C23 H23A 1.079(12) . ?
C23 H23B 0.92(2) . ?
C23 H24C 1.53(7) . ?
C22 C22A 1.41(2) . ?
C22 C23A 1.47(2) . ?
C22 H22A 0.87(2) . ?
C22 H22B 0.963(16) . ?
C22 H22C 1.57(8) . ?
C23A H23A 1.061(10) . ?
C23A H22B 0.92(2) . ?
C23A H23C 0.82(2) . ?
C24 H24A 1.03(2) . ?
C24 H23B 0.92(2) . ?
C24 H24C 0.78(2) . ?
C22A H22A 0.87(2) . ?
C22A H24B 1.02(2) . ?
C22A H22C 0.87(2) . ?

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
C3 C15 C16 120.5(2) . . ?
C3 C15 C13 119.3(2) . . ?
C16 C15 C13 120.2(2) . . ?
O3 N2 O4 124.9(4) . . ?
O3 N2 C29 117.8(3) . . ?
O4 N2 C29 117.2(3) . . ?
C10 C16 C6 119.3(2) . . ?
C10 C16 C15 120.6(2) . . ?
C6 C16 C15 120.2(2) . . ?
C7 C6 C16 118.9(2) . . ?
C7 C6 C5 123.0(2) . . ?
C16 C6 C5 118.2(2) . . ?
C2 C3 C15 119.3(2) . . ?
C2 C3 C4 122.5(2) . . ?
C15 C3 C4 118.2(2) . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C2 C1 C14 117.6(2) . . ?
C2 C1 C17 122.0(2) . . ?
C14 C1 C17 120.4(2) . . ?
C14 C13 C15 118.8(2) . . ?
C14 C13 C12 123.3(2) . . ?
C15 C13 C12 117.9(2) . . ?
C1 C2 C3 122.3(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C9 C10 C16 119.4(2) . . ?
C9 C10 C11 122.7(2) . . ?
C16 C10 C11 118.0(2) . . ?
C8 C7 C6 122.6(3) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C13 C14 C1 122.7(2) . . ?
C13 C14 H14 118.7 . . ?
C1 C14 H14 118.7 . . ?
C7 C8 C9 117.6(2) . . ?
C7 C8 C21 121.1(3) . . ?
C9 C8 C21 121.3(3) . . ?
O1 N1 O2 124.6(5) . . ?
O1 N1 C25 117.6(5) . . ?
O2 N1 C25 117.7(4) . . ?
C10 C9 C8 122.3(3) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C11 C12 C13 121.8(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C18 C17 C19 109.4(3) . . ?
C18 C17 C20 108.2(3) . . ?
C19 C17 C20 106.7(3) . . ?
C18 C17 C1 109.1(3) . . ?
C19 C17 C1 110.9(3) . . ?
C20 C17 C1 112.5(3) . . ?
C28 C29 C30 123.1(3) . . ?
C28 C29 N2 118.7(3) . . ?
C30 C29 N2 118.1(3) . . ?
C25 C30 C29 117.1(3) . . ?
C25 C30 H30 121.4 . . ?
C29 C30 H30 121.4 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C23 C21 C22A 143.6(6) . . ?
C23 C21 C8 109.5(4) . . ?
C22A C21 C8 106.9(4) . . ?
C23 C21 C24 53.6(10) . . ?
C22A C21 C24 111.9(8) . . ?
C8 C21 C24 112.1(4) . . ?
C23 C21 C23A 59.3(10) . . ?
C22A C21 C23A 109.1(8) . . ?
C8 C21 C23A 106.9(4) . . ?
C24 C21 C23A 109.8(8) . . ?
C23 C21 C24A 111.2(10) . . ?
C22A C21 C24A 55.5(9) . . ?
C8 C21 C24A 109.3(4) . . ?
C24 C21 C24A 59.9(9) . . ?
C23A C21 C24A 143.6(5) . . ?
C23 C21 C22 109.5(9) . . ?
C22A C21 C22 53.8(9) . . ?
C8 C21 C22 112.8(4) . . ?
C24 C21 C22 135.2(5) . . ?
C23A C21 C22 56.0(9) . . ?
C24A C21 C22 104.5(8) . . ?
C30 C25 C26 122.0(4) . . ?
C30 C25 N1 117.6(4) . . ?
C26 C25 N1 120.3(4) . . ?
C29 C28 C27 118.1(4) . . ?
C29 C28 H28 120.9 . . ?
C27 C28 H28 120.9 . . ?
C27 C26 C25 118.6(4) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C28 C27 C26 121.0(4) . . ?
C28 C27 H29 119.5 . . ?
C26 C27 H29 119.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22A C24A C24 117.1(9) . . ?
C22A C24A C21 61.2(6) . . ?
C24 C24A C21 59.7(6) . . ?
C22A C24A H24A 154(3) . . ?
C24 C24A H24A 41.2(16) . . ?
C21 C24A H24A 93(3) . . ?
C22A C24A H24B 45.3(15) . . ?
C24 C24A H24B 157(3) . . ?
C21 C24A H24B 98(3) . . ?
H24A C24A H24B 148(4) . . ?
C22A C24A H22C 34.0(15) . . ?
C24 C24A H22C 109(3) . . ?
C21 C24A H22C 75(3) . . ?
H24A C24A H22C 147(4) . . ?
H24B C24A H22C 65(3) . . ?
C24 C23 C23A 121.4(10) . . ?
C24 C23 C21 64.1(7) . . ?
C23A C23 C21 61.3(7) . . ?
C24 C23 H23A 161(3) . . ?
C23A C23 H23A 44.3(10) . . ?
C21 C23 H23A 97(2) . . ?
C24 C23 H23B 41.4(18) . . ?
C23A C23 H23B 160(4) . . ?
C21 C23 H23B 99(4) . . ?
H23A C23 H23B 148(4) . . ?
C24 C23 H24C 30.5(15) . . ?
C23A C23 H24C 114(3) . . ?
C21 C23 H24C 76(3) . . ?
H23A C23 H24C 154(3) . . ?
H23B C23 H24C 58(4) . . ?
C22A C22 C23A 120.9(9) . . ?
C22A C22 C21 60.9(6) . . ?
C23A C22 C21 60.8(6) . . ?
C22A C22 H22A 36(2) . . ?
C23A C22 H22A 151(6) . . ?
C21 C22 H22A 92(5) . . ?
C22A C22 H22B 151(5) . . ?
C23A C22 H22B 37.3(18) . . ?
C21 C22 H22B 92(3) . . ?
H22A C22 H22B 150(8) . . ?
C22A C22 H22C 33.3(17) . . ?
C23A C22 H22C 116(3) . . ?
C21 C22 H22C 72(3) . . ?
H22A C22 H22C 56(6) . . ?
H22B C22 H22C 152(4) . . ?
C22 C23A C23 116.0(9) . . ?
C22 C23A C21 63.2(6) . . ?
C23 C23A C21 59.4(6) . . ?
C22 C23A H23A 159(2) . . ?
C23 C23A H23A 45.3(11) . . ?
C21 C23A H23A 96(2) . . ?
C22 C23A H22B 39.6(16) . . ?
C23 C23A H22B 155(3) . . ?
C21 C23A H22B 96(4) . . ?
H23A C23A H22B 156(4) . . ?
C22 C23A H23C 86(6) . . ?
C23 C23A H23C 82(6) . . ?
C21 C23A H23C 103(6) . . ?
H23A C23A H23C 97(7) . . ?
H22B C23A H23C 99(7) . . ?
C23 C24 C24A 119.9(10) . . ?
C23 C24 C21 62.3(7) . . ?
C24A C24 C21 60.4(6) . . ?
C23 C24 H24A 155(3) . . ?
C24A C24 H24A 41.0(16) . . ?
C21 C24 H24A 94(3) . . ?
C23 C24 H23B 41.1(18) . . ?
C24A C24 H23B 157(4) . . ?
C21 C24 H23B 97(4) . . ?
H24A C24 H23B 149(5) . . ?
C23 C24 H24C 85(6) . . ?
C24A C24 H24C 90(6) . . ?
C21 C24 H24C 102(6) . . ?
H24A C24 H24C 107(7) . . ?
H23B C24 H24C 99(7) . . ?
C22 C22A C24A 121.9(10) . . ?
C22 C22A C21 65.4(7) . . ?
C24A C22A C21 63.4(7) . . ?
C22 C22A H22A 36(2) . . ?
C24A C22A H22A 158(3) . . ?
C21 C22A H22A 96(5) . . ?
C22 C22A H24B 165(3) . . ?
C24A C22A H24B 45.2(15) . . ?
C21 C22A H24B 100(3) . . ?
H22A C22A H24B 155(4) . . ?
C22 C22A H22C 84(6) . . ?
C24A C22A H22C 78(6) . . ?
C21 C22A H22C 98(6) . . ?
H22A C22A H22C 98(8) . . ?
H24B C22A H22C 98(7) . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        78.53
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.290
_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_Cocrystal2
_database_code_depnum_ccdc_archive 'CCDC 1840881'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
_audit_creation_date             2018-01-21
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H26, C10 H2 N4'
_chemical_formula_sum            'C34 H28 N4'
_chemical_formula_weight         492.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H20 N4 '
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 1 2/m 1'
_space_group_name_Hall           '-I 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   15.3925(6)
_cell_length_b                   6.8374(3)
_cell_length_c                   12.8802(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.087(3)
_cell_angle_gamma                90.00
_cell_volume                     1353.61(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2825
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      76.4970
_cell_measurement_theta_min      4.5960
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5444
_diffrn_reflns_theta_full        76.97
_diffrn_reflns_theta_max         76.97
_diffrn_reflns_theta_min         4.36
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  28.00   0.50    0.50    --  -38.50  38.00-174.00  140
  2  ω   -105.00 -35.00   0.50    0.50    --  -38.50 -38.00  29.00  140
  3  ω     46.00 116.00   0.50    0.50    --   49.31  38.00-174.00  140
  4  ω    -17.00  53.00   0.50    0.50    --   49.31 -38.00  29.00  140
  5  ω     40.00 110.00   0.50    2.50    --  106.38 -38.00  29.00  140
  6  ω    103.00 173.00   0.50    2.50    --  106.38  38.00-174.00  140
  7  ω    -17.00  53.00   0.50    0.50    --   49.31 -37.00 -90.00  140
  8  ω     46.00 116.00   0.50    0.50    --   49.31  37.00-120.00  140
  9  ω     44.00 120.00   0.50    2.50    --  106.38 -61.00 120.00  152
 10  ω     42.00 130.00   0.50    2.50    --  106.38 -77.00 -60.00  176
 11  ω    102.00 171.00   0.50    2.50    --  106.38  45.00 150.00  138
 12  ω     94.00 171.00   0.50    2.50    --  106.38 125.00  60.00  154
 13  ω    102.00 171.00   0.50    2.50    --  106.38  45.00-150.00  138
 14  ω    102.00 171.00   0.50    2.50    --  106.38  45.00  60.00  138
 15  ω     38.00 109.00   0.50    2.50    --  106.38 -94.00-120.00  142
 16  ω     38.00 110.00   0.50    2.50    --  106.38 -30.00-120.00  144
 17  ω     38.00 112.00   0.50    0.50    --   49.31  57.00  90.00  148
 18  ω     26.00  51.00   0.50    0.50    --   49.31  77.00 -90.00   50
 19  ω     26.00 114.00   0.50    0.50    --   49.31  77.00 -30.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0304464000
_diffrn_orient_matrix_UB_12      0.0345613000
_diffrn_orient_matrix_UB_13      0.1105082000
_diffrn_orient_matrix_UB_21      0.0833922000
_diffrn_orient_matrix_UB_22      -0.0987642000
_diffrn_orient_matrix_UB_23      0.0460038000
_diffrn_orient_matrix_UB_31      0.0465833000
_diffrn_orient_matrix_UB_32      0.1995311000
_diffrn_orient_matrix_UB_33      0.0037349000
_diffrn_oxdiff_ac3_digest_frames 
;
015e1e73e4907bc1a8e5080cf66833bedf00038997e
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01b1273b102b56eb642bdb6dca03ab4092d247
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1184
_reflns_number_total             1518
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0027(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1623
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C5 C 0.45362(10) 0.5000 0.49831(12) 0.0403(4) Uani 1 d . . 2 S T P
C6 C 0.40565(11) 0.5000 0.40146(13) 0.0441(4) Uani 1 d . . 2 S T P
C4 C 0.40900(11) 0.5000 0.59167(13) 0.0438(4) Uani 1 d . . 2 S T P
C8 C 0.54062(12) 0.5000 0.31126(14) 0.0504(5) Uani 1 d . . 2 S T P
C7 C 0.45257(12) 0.5000 0.30791(14) 0.0502(5) Uani 1 d . . 2 S T P
C1 C 0.31461(12) 0.5000 0.40003(15) 0.0508(5) Uani 1 d . . 2 S T P
C3 C 0.31811(12) 0.5000 0.58572(15) 0.0507(5) Uani 1 d . . 2 S T P
N1 N 0.26078(17) 0.0000 0.36777(17) 0.0843(6) Uani 1 d . . 2 S T P
C2 C 0.26988(11) 0.5000 0.49099(15) 0.0526(5) Uani 1 d . . 2 S T P
C15 C 0.57051(14) 0.0000 0.43724(14) 0.0553(5) Uani 1 d . . 2 S T P
C12 C 0.48726(15) 0.0000 0.39242(15) 0.0574(6) Uani 1 d . . 2 S T P
N2 N 0.70054(16) 0.0000 0.31928(16) 0.0862(7) Uani 1 d . . 2 S T P
C13 C 0.41591(14) 0.0000 0.45422(14) 0.0558(5) Uani 1 d . . 2 S T P
C16 C 0.64348(15) 0.0000 0.37205(16) 0.0641(6) Uani 1 d . . 2 S T P
C9 C 0.16976(12) 0.5000 0.49085(17) 0.0610(6) Uani 1 d . . 2 S T P
C14 C 0.32922(17) 0.0000 0.40682(16) 0.0642(6) Uani 1 d . . 2 S T P
C11 C 0.13985(11) 0.6829(3) 0.54745(17) 0.0776(6) Uani 1 d . . 1 . . .
C10 C 0.12850(16) 0.5000 0.3800(2) 0.0818(8) Uani 1 d . . 2 S T P
H3 H 0.2930(15) 0.5000 0.650(2) 0.061(6) Uiso 1 d . . 2 S T P
H7 H 0.4185(14) 0.5000 0.2405(19) 0.057(6) Uiso 1 d . . 2 S T P
H1 H 0.2814(15) 0.5000 0.3331(19) 0.058(6) Uiso 1 d . . 2 S T P
H11A H 0.0747(13) 0.685(3) 0.5480(14) 0.084(6) Uiso 1 d . . 1 . . .
H12 H 0.4772(15) 0.0000 0.317(2) 0.067(6) Uiso 1 d . . 2 S T P
H11B H 0.1565(14) 0.806(4) 0.5098(18) 0.108(7) Uiso 1 d . . 1 . . .
H11C H 0.1665(15) 0.687(3) 0.6225(18) 0.100(6) Uiso 1 d . . 1 . . .
H8 H 0.5724(16) 0.5000 0.247(2) 0.069(6) Uiso 1 d . . 2 S T P
H10A H 0.1456(13) 0.375(3) 0.3449(16) 0.085(5) Uiso 1 d . . 1 . . .
H10B H 0.065(2) 0.5000 0.383(2) 0.099(9) Uiso 1 d . . 2 S T 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
C5 C5 1.426(3) 5_666 ?
C5 C6 1.415(3) . ?
C5 C4 1.417(2) . ?
C6 C7 1.438(2) . ?
C6 C1 1.400(3) . ?
C4 C8 1.435(3) 5_666 ?
C4 C3 1.397(2) . ?
C8 C4 1.435(3) 5_666 ?
C8 C7 1.354(3) . ?
C8 H8 0.98(3) . ?
C7 H7 0.99(2) . ?
C1 C2 1.390(3) . ?
C1 H1 0.98(2) . ?
C3 C2 1.394(3) . ?
C3 H3 0.93(3) . ?
N1 C14 1.143(3) . ?
C2 C9 1.541(3) . ?
C15 C12 1.377(3) . ?
C15 C13 1.402(3) 5_656 ?
C15 C16 1.438(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.98(2) . ?
N2 C16 1.139(3) . ?
C13 C15 1.403(3) 5_656 ?
C13 C14 1.437(3) . ?
C9 C11 1.531(2) . ?
C9 C11 1.531(2) 6_565 ?
C9 C10 1.531(3) . ?
C11 H11A 1.00(2) . ?
C11 H11B 1.01(2) . ?
C11 H11C 1.03(2) . ?
C10 H10A 1.01(2) . ?
C10 H10B 0.98(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
C6 C5 C5 120.06(18) . 5_666 ?
C6 C5 C4 119.64(16) . . ?
C4 C5 C5 120.30(19) . 5_666 ?
C5 C6 C7 118.49(16) . . ?
C1 C6 C5 119.07(16) . . ?
C1 C6 C7 122.44(17) . . ?
C5 C4 C8 118.40(16) . 5_666 ?
C3 C4 C5 118.90(16) . . ?
C3 C4 C8 122.70(16) . 5_666 ?
C4 C8 H8 117.5(14) 5_666 . ?
C7 C8 C4 121.39(17) . 5_666 ?
C7 C8 H8 121.2(14) . . ?
C6 C7 H7 118.0(13) . . ?
C8 C7 C6 121.37(17) . . ?
C8 C7 H7 120.7(13) . . ?
C6 C1 H1 119.1(13) . . ?
C2 C1 C6 121.97(18) . . ?
C2 C1 H1 118.9(13) . . ?
C4 C3 H3 114.4(15) . . ?
C2 C3 C4 122.19(17) . . ?
C2 C3 H3 123.4(15) . . ?
C1 C2 C3 118.24(17) . . ?
C1 C2 C9 122.65(17) . . ?
C3 C2 C9 119.11(17) . . ?
C12 C15 C13 120.22(19) . 5_656 ?
C12 C15 C16 119.59(18) . . ?
C13 C15 C16 120.2(2) 5_656 . ?
C15 C12 C13 120.39(18) . . ?
C15 C12 H12 120.7(14) . . ?
C13 C12 H12 118.9(14) . . ?
C15 C13 C14 120.56(19) 5_656 . ?
C12 C13 C15 119.4(2) . 5_656 ?
C12 C13 C14 120.05(17) . . ?
N2 C16 C15 179.1(2) . . ?
C11 C9 C2 109.02(12) 6_565 . ?
C11 C9 C2 109.02(12) . . ?
C11 C9 C11 109.6(2) . 6_565 ?
C11 C9 C10 108.89(13) . . ?
C11 C9 C10 108.89(13) 6_565 . ?
C10 C9 C2 111.44(17) . . ?
N1 C14 C13 179.0(2) . . ?
C9 C11 H11A 109.8(11) . . ?
C9 C11 H11B 111.1(13) . . ?
C9 C11 H11C 110.9(12) . . ?
H11A C11 H11B 105.9(16) . . ?
H11A C11 H11C 109.9(17) . . ?
H11B C11 H11C 109.1(18) . . ?
C9 C10 H10A 108.2(11) . . ?
C9 C10 H10B 109.4(19) . . ?
H10A C10 H10B 107.4(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.076
_oxdiff_exptl_absorpt_empirical_full_min 0.306
