# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_P21_a
_database_code_depnum_ccdc_archive 'CCDC 1897962'
loop_
_audit_author_name
_audit_author_address
'Osamu Kitagawa'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 Cl N2 O'
_chemical_formula_sum            'C15 H11 Cl N2 O'
_chemical_formula_weight         270.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.8518(2)
_cell_length_b                   15.3215(3)
_cell_length_c                   10.3543(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.2740(10)
_cell_angle_gamma                90
_cell_volume                     1290.01(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.5204
_cell_measurement_theta_max      25.0482

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.629
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.361
_exptl_absorpt_coefficient_mu    0.288
_shelx_estimated_absorpt_T_min   0.840
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            14814
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_full        25.023
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4513
_reflns_number_gt                4413
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.980

_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       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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)+(0.0307P)²+0.1589P] 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 2049 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4513
_refine_ls_number_parameters     345
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0558
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.6466(3) 0.40297(14) 0.4910(2) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.5402(2) 0.47891(14) 0.4721(2) 0.0181(4) Uani 1 1 d . . . . .
C3 C 0.3702(3) 0.47100(14) 0.3966(2) 0.0225(5) Uani 1 1 d . . . . .
H3 H 0.323429 0.416297 0.358011 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2713(3) 0.54328(16) 0.3787(2) 0.0280(5) Uani 1 1 d . . . . .
H4 H 0.155729 0.538398 0.328328 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3408(3) 0.62366(15) 0.4344(2) 0.0279(5) Uani 1 1 d . . . . .
H5 H 0.271822 0.673294 0.420402 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5082(3) 0.63229(15) 0.5096(2) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.553897 0.687354 0.547166 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6101(2) 0.55895(13) 0.5301(2) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.8731(3) 0.50256(13) 0.6244(2) 0.0179(4) Uani 1 1 d . . . . .
C9 C 1.0542(3) 0.51245(15) 0.7046(2) 0.0281(5) Uani 1 1 d . . . . .
H9A H 1.079222 0.573013 0.736262 0.042 Uiso 1 1 calc R U . . .
H9B H 1.111501 0.497289 0.643773 0.042 Uiso 1 1 calc R U . . .
H9C H 1.090641 0.473527 0.786336 0.042 Uiso 1 1 calc R U . . .
C10 C 0.9249(2) 0.34940(13) 0.5791(2) 0.0177(4) Uani 1 1 d . . . . .
C11 C 0.9727(2) 0.33330(14) 0.4683(2) 0.0205(4) Uani 1 1 d . . . . .
C12 C 1.0699(3) 0.26188(14) 0.4715(2) 0.0238(5) Uani 1 1 d . . . . .
H12 H 1.101290 0.250612 0.395322 0.029 Uiso 1 1 calc R U . . .
C13 C 1.1208(3) 0.20715(14) 0.5871(2) 0.0234(5) Uani 1 1 d . . . . .
H13 H 1.187167 0.157868 0.589866 0.028 Uiso 1 1 calc R U . . .
C14 C 1.0762(3) 0.22334(14) 0.6991(2) 0.0218(4) Uani 1 1 d . . . . .
H14 H 1.112995 0.185780 0.778572 0.026 Uiso 1 1 calc R U . . .
C15 C 0.9774(2) 0.29472(13) 0.6946(2) 0.0188(4) Uani 1 1 d . . . . .
H15 H 0.945961 0.305904 0.770766 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8534(2) 0.56428(14) 0.9778(2) 0.0199(4) Uani 1 1 d . . . . .
C17 C 0.9528(2) 0.64037(13) 0.9784(2) 0.0171(4) Uani 1 1 d . . . . .
C18 C 1.1246(2) 0.63535(14) 1.0401(2) 0.0203(4) Uani 1 1 d . . . . .
H18 H 1.177234 0.581753 1.078453 0.024 Uiso 1 1 calc R U . . .
C19 C 1.2173(2) 0.70884(13) 1.0450(2) 0.0203(4) Uani 1 1 d . . . . .
H19 H 1.333926 0.705843 1.087451 0.024 Uiso 1 1 calc R U . . .
C20 C 1.1401(3) 0.78742(14) 0.9877(2) 0.0213(4) Uani 1 1 d . . . . .
H20 H 1.204581 0.837603 0.991033 0.026 Uiso 1 1 calc R U . . .
C21 C 0.9703(3) 0.79271(13) 0.9262(2) 0.0195(4) Uani 1 1 d . . . . .
H21 H 0.918772 0.846370 0.886986 0.023 Uiso 1 1 calc R U . . .
C22 C 0.8745(2) 0.71939(13) 0.9216(2) 0.0166(4) Uani 1 1 d . . . . .
C23 C 0.6155(2) 0.66074(13) 0.8625(2) 0.0172(4) Uani 1 1 d . . . . .
C24 C 0.4323(3) 0.66873(15) 0.8034(2) 0.0229(5) Uani 1 1 d . . . . .
H24A H 0.400132 0.726377 0.760257 0.034 Uiso 1 1 calc R U . . .
H24B H 0.393106 0.661649 0.879060 0.034 Uiso 1 1 calc R U . . .
H24C H 0.383633 0.623407 0.732227 0.034 Uiso 1 1 calc R U . . .
C25 C 0.5811(2) 0.50666(13) 0.9186(2) 0.0185(4) Uani 1 1 d . . . . .
C26 C 0.5382(2) 0.49173(14) 1.0323(2) 0.0188(4) Uani 1 1 d . . . . .
C27 C 0.4502(3) 0.41808(14) 1.0376(2) 0.0224(5) Uani 1 1 d . . . . .
H27 H 0.423697 0.407685 1.116656 0.027 Uiso 1 1 calc R U . . .
C28 C 0.4011(3) 0.35981(14) 0.9266(2) 0.0247(5) Uani 1 1 d . . . . .
H28 H 0.341194 0.308988 0.929754 0.030 Uiso 1 1 calc R U . . .
C29 C 0.4388(3) 0.37506(14) 0.8109(2) 0.0253(5) Uani 1 1 d . . . . .
H29 H 0.402173 0.335711 0.733737 0.030 Uiso 1 1 calc R U . . .
C30 C 0.5301(3) 0.44799(14) 0.8082(2) 0.0233(5) Uani 1 1 d . . . . .
H30 H 0.557945 0.457754 0.729645 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 0.90673(7) 0.40242(3) 0.32424(5) 0.02769(15) Uani 1 1 d . . . . .
Cl2 Cl 0.59633(6) 0.56625(3) 1.16974(5) 0.02368(13) Uani 1 1 d . . . . .
N1 N 0.7783(2) 0.56957(11) 0.60947(17) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.8143(2) 0.42062(10) 0.56910(17) 0.0166(4) Uani 1 1 d . . . . .
N3 N 0.7034(2) 0.72780(11) 0.86211(17) 0.0179(4) Uani 1 1 d . . . . .
N4 N 0.6832(2) 0.57960(11) 0.91742(17) 0.0169(4) Uani 1 1 d . . . . .
O1 O 0.60183(18) 0.33012(10) 0.44607(16) 0.0270(3) Uani 1 1 d . . . . .
O2 O 0.90748(19) 0.49311(10) 1.02669(18) 0.0301(4) 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 O1 1.214(3) . ?
C1 N2 1.408(3) . ?
C1 C2 1.461(3) . ?
C2 C7 1.398(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(3) . ?
C6 H6 0.9500 . ?
C7 N1 1.397(3) . ?
C8 N1 1.296(3) . ?
C8 N2 1.393(3) . ?
C8 C9 1.493(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.381(3) . ?
C10 C11 1.393(3) . ?
C10 N2 1.442(2) . ?
C11 C12 1.384(3) . ?
C11 Cl1 1.732(2) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O2 1.218(3) . ?
C16 N4 1.404(3) . ?
C16 C17 1.459(3) . ?
C17 C18 1.400(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(3) . ?
C21 H21 0.9500 . ?
C22 N3 1.397(3) . ?
C23 N3 1.290(3) . ?
C23 N4 1.399(3) . ?
C23 C24 1.495(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C30 1.382(3) . ?
C25 C26 1.392(3) . ?
C25 N4 1.440(3) . ?
C26 C27 1.385(3) . ?
C26 Cl2 1.736(2) . ?
C27 C28 1.383(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.384(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 120.49(19) . . ?
O1 C1 C2 125.83(19) . . ?
N2 C1 C2 113.68(18) . . ?
C7 C2 C3 120.78(19) . . ?
C7 C2 C1 119.24(18) . . ?
C3 C2 C1 119.98(19) . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
N1 C7 C2 122.89(17) . . ?
N1 C7 C6 117.89(18) . . ?
C2 C7 C6 119.22(18) . . ?
N1 C8 N2 123.08(18) . . ?
N1 C8 C9 119.22(18) . . ?
N2 C8 C9 117.70(18) . . ?
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 . . ?
C15 C10 C11 119.86(18) . . ?
C15 C10 N2 120.51(18) . . ?
C11 C10 N2 119.56(18) . . ?
C12 C11 C10 120.55(18) . . ?
C12 C11 Cl1 119.94(15) . . ?
C10 C11 Cl1 119.49(16) . . ?
C13 C12 C11 119.15(19) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.73(19) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 119.90(18) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
O2 C16 N4 120.76(19) . . ?
O2 C16 C17 125.17(18) . . ?
N4 C16 C17 114.05(18) . . ?
C18 C17 C22 120.43(18) . . ?
C18 C17 C16 120.19(18) . . ?
C22 C17 C16 119.34(18) . . ?
C19 C18 C17 119.60(18) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.23(19) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.43(19) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.20(19) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
N3 C22 C21 118.60(17) . . ?
N3 C22 C17 122.29(17) . . ?
C21 C22 C17 119.10(18) . . ?
N3 C23 N4 123.15(18) . . ?
N3 C23 C24 119.46(18) . . ?
N4 C23 C24 117.39(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 118.94(19) . . ?
C30 C25 N4 119.91(18) . . ?
C26 C25 N4 121.10(18) . . ?
C27 C26 C25 120.9(2) . . ?
C27 C26 Cl2 119.54(16) . . ?
C25 C26 Cl2 119.59(16) . . ?
C28 C27 C26 119.4(2) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C27 C28 C29 120.42(19) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C30 119.7(2) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C25 C30 C29 120.6(2) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C8 N1 C7 117.86(17) . . ?
C8 N2 C1 123.20(16) . . ?
C8 N2 C10 121.30(16) . . ?
C1 N2 C10 115.32(16) . . ?
C23 N3 C22 118.38(17) . . ?
C23 N4 C16 122.77(17) . . ?
C23 N4 C25 121.55(16) . . ?
C16 N4 C25 115.66(16) . . ?

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
O1 C1 C2 C7 -179.88(19) . . . . ?
N2 C1 C2 C7 0.1(3) . . . . ?
O1 C1 C2 C3 0.1(3) . . . . ?
N2 C1 C2 C3 -179.93(17) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C3 C4 -179.52(19) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C3 C2 C7 N1 178.21(17) . . . . ?
C1 C2 C7 N1 -1.8(3) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C1 C2 C7 C6 178.78(17) . . . . ?
C5 C6 C7 N1 -178.52(18) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
N2 C10 C11 C12 -175.68(18) . . . . ?
C15 C10 C11 Cl1 -179.83(15) . . . . ?
N2 C10 C11 Cl1 3.2(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
Cl1 C11 C12 C13 -179.68(17) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
N2 C10 C15 C14 176.23(18) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
O2 C16 C17 C18 -0.8(3) . . . . ?
N4 C16 C17 C18 177.64(17) . . . . ?
O2 C16 C17 C22 -178.4(2) . . . . ?
N4 C16 C17 C22 0.1(3) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C16 C17 C18 C19 -177.44(19) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 N3 178.25(18) . . . . ?
C20 C21 C22 C17 -0.8(3) . . . . ?
C18 C17 C22 N3 -178.42(17) . . . . ?
C16 C17 C22 N3 -0.9(3) . . . . ?
C18 C17 C22 C21 0.6(3) . . . . ?
C16 C17 C22 C21 178.11(17) . . . . ?
C30 C25 C26 C27 1.9(3) . . . . ?
N4 C25 C26 C27 -175.24(18) . . . . ?
C30 C25 C26 Cl2 -178.25(16) . . . . ?
N4 C25 C26 Cl2 4.6(3) . . . . ?
C25 C26 C27 C28 -1.5(3) . . . . ?
Cl2 C26 C27 C28 178.66(16) . . . . ?
C26 C27 C28 C29 -0.3(3) . . . . ?
C27 C28 C29 C30 1.8(3) . . . . ?
C26 C25 C30 C29 -0.5(3) . . . . ?
N4 C25 C30 C29 176.73(19) . . . . ?
C28 C29 C30 C25 -1.4(3) . . . . ?
N2 C8 N1 C7 -2.1(3) . . . . ?
C9 C8 N1 C7 177.97(18) . . . . ?
C2 C7 N1 C8 2.9(3) . . . . ?
C6 C7 N1 C8 -177.76(18) . . . . ?
N1 C8 N2 C1 0.5(3) . . . . ?
C9 C8 N2 C1 -179.64(18) . . . . ?
N1 C8 N2 C10 175.34(18) . . . . ?
C9 C8 N2 C10 -4.8(3) . . . . ?
O1 C1 N2 C8 -179.41(19) . . . . ?
C2 C1 N2 C8 0.6(3) . . . . ?
O1 C1 N2 C10 5.4(3) . . . . ?
C2 C1 N2 C10 -174.59(17) . . . . ?
C15 C10 N2 C8 88.7(2) . . . . ?
C11 C10 N2 C8 -94.3(2) . . . . ?
C15 C10 N2 C1 -96.0(2) . . . . ?
C11 C10 N2 C1 80.9(2) . . . . ?
N4 C23 N3 C22 -1.2(3) . . . . ?
C24 C23 N3 C22 178.18(17) . . . . ?
C21 C22 N3 C23 -177.60(18) . . . . ?
C17 C22 N3 C23 1.4(3) . . . . ?
N3 C23 N4 C16 0.4(3) . . . . ?
C24 C23 N4 C16 -178.95(17) . . . . ?
N3 C23 N4 C25 178.73(17) . . . . ?
C24 C23 N4 C25 -0.6(3) . . . . ?
O2 C16 N4 C23 178.69(19) . . . . ?
C17 C16 N4 C23 0.1(3) . . . . ?
O2 C16 N4 C25 0.3(3) . . . . ?
C17 C16 N4 C25 -178.28(16) . . . . ?
C30 C25 N4 C23 92.6(2) . . . . ?
C26 C25 N4 C23 -90.3(2) . . . . ?
C30 C25 N4 C16 -89.0(2) . . . . ?
C26 C25 N4 C16 88.2(2) . . . . ?

_refine_diff_density_max         0.128
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_P21c_a
_database_code_depnum_ccdc_archive 'CCDC 1897963'
loop_
_audit_author_name
_audit_author_address
'Osamu Kitagawa'
;Shibaura Institute of technology
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 Cl N2 O'
_chemical_formula_sum            'C15 H11 Cl N2 O'
_chemical_formula_weight         270.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   17.616(3)
_cell_length_b                   5.6004(10)
_cell_length_c                   12.779(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.051(6)
_cell_angle_gamma                90
_cell_volume                     1248.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    122
_cell_measurement_theta_min      3.4772
_cell_measurement_theta_max      21.5920

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    0.298
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            10023
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.220
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2194
_reflns_number_gt                1623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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)+(0.0389P)²+1.4960P] 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_number_reflns         2194
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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 0.2443(2) 0.4613(6) 0.7178(3) 0.0222(8) Uani 1 1 d . . . . .
C2 C 0.17233(19) 0.3307(6) 0.7048(3) 0.0226(8) Uani 1 1 d . . . . .
C3 C 0.1589(2) 0.1535(6) 0.7781(3) 0.0278(9) Uani 1 1 d . . . . .
H3 H 0.195484 0.126099 0.838976 0.033 Uiso 1 1 calc R U . . .
C4 C 0.0929(2) 0.0204(7) 0.7616(3) 0.0320(9) Uani 1 1 d . . . . .
H4 H 0.083741 -0.099420 0.810915 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0393(2) 0.0612(7) 0.6721(3) 0.0292(9) Uani 1 1 d . . . . .
H5 H -0.005731 -0.034126 0.660239 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0505(2) 0.2362(6) 0.6012(3) 0.0273(8) Uani 1 1 d . . . . .
H6 H 0.013078 0.263064 0.541226 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1172(2) 0.3763(6) 0.6169(2) 0.0233(8) Uani 1 1 d . . . . .
C8 C 0.1907(2) 0.6731(6) 0.5562(2) 0.0224(8) Uani 1 1 d . . . . .
C9 C 0.2020(2) 0.8732(6) 0.4823(3) 0.0281(9) Uani 1 1 d . . . . .
H9A H 0.153884 0.904061 0.435907 0.042 Uiso 1 1 calc R U . . .
H9B H 0.241890 0.829214 0.439548 0.042 Uiso 1 1 calc R U . . .
H9C H 0.217744 1.017254 0.523238 0.042 Uiso 1 1 calc R U . . .
C10 C 0.32420(19) 0.7371(6) 0.6368(2) 0.0217(8) Uani 1 1 d . . . . .
C11 C 0.3753(2) 0.6577(6) 0.5701(3) 0.0240(8) Uani 1 1 d . . . . .
C12 C 0.4458(2) 0.7676(7) 0.5715(3) 0.0310(9) Uani 1 1 d . . . . .
H12 H 0.480374 0.713878 0.525858 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4655(2) 0.9561(7) 0.6398(3) 0.0336(9) Uani 1 1 d . . . . .
H13 H 0.513801 1.032176 0.640615 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4158(2) 1.0349(7) 0.7068(3) 0.0323(9) Uani 1 1 d . . . . .
H14 H 0.429852 1.163785 0.753882 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3453(2) 0.9251(7) 0.7049(3) 0.0284(8) Uani 1 1 d . . . . .
H15 H 0.311018 0.979228 0.750960 0.034 Uiso 1 1 calc R U . . .
Cl1 Cl 0.34969(5) 0.42097(16) 0.48439(7) 0.0292(3) Uani 1 1 d . . . . .
N1 N 0.12642(16) 0.5564(5) 0.5440(2) 0.0242(7) Uani 1 1 d . . . . .
N2 N 0.25117(15) 0.6239(5) 0.6365(2) 0.0209(6) Uani 1 1 d . . . . .
O1 O 0.29728(13) 0.4342(4) 0.79070(17) 0.0263(6) 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 O1 1.232(4) . ?
C1 N2 1.400(4) . ?
C1 C2 1.452(5) . ?
C2 C7 1.402(5) . ?
C2 C3 1.408(5) . ?
C3 C4 1.372(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.368(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(5) . ?
C6 H6 0.9500 . ?
C7 N1 1.397(4) . ?
C8 N1 1.297(4) . ?
C8 N2 1.399(4) . ?
C8 C9 1.496(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.384(5) . ?
C10 C11 1.395(5) . ?
C10 N2 1.434(4) . ?
C11 C12 1.384(5) . ?
C11 Cl1 1.739(4) . ?
C12 C13 1.383(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 120.4(3) . . ?
O1 C1 C2 125.5(3) . . ?
N2 C1 C2 114.0(3) . . ?
C7 C2 C3 120.0(3) . . ?
C7 C2 C1 119.7(3) . . ?
C3 C2 C1 120.3(3) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
N1 C7 C2 122.2(3) . . ?
N1 C7 C6 118.8(3) . . ?
C2 C7 C6 119.0(3) . . ?
N1 C8 N2 123.4(3) . . ?
N1 C8 C9 119.6(3) . . ?
N2 C8 C9 117.0(3) . . ?
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 . . ?
C15 C10 C11 119.2(3) . . ?
C15 C10 N2 120.0(3) . . ?
C11 C10 N2 120.8(3) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 Cl1 120.0(3) . . ?
C10 C11 Cl1 119.7(3) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C10 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C8 N1 C7 117.7(3) . . ?
C8 N2 C1 122.4(3) . . ?
C8 N2 C10 120.4(3) . . ?
C1 N2 C10 117.2(3) . . ?

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
O1 C1 C2 C7 -178.9(3) . . . . ?
N2 C1 C2 C7 -0.7(4) . . . . ?
O1 C1 C2 C3 -1.0(5) . . . . ?
N2 C1 C2 C3 177.1(3) . . . . ?
C7 C2 C3 C4 2.1(5) . . . . ?
C1 C2 C3 C4 -175.8(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C3 C2 C7 N1 177.5(3) . . . . ?
C1 C2 C7 N1 -4.7(5) . . . . ?
C3 C2 C7 C6 -2.6(5) . . . . ?
C1 C2 C7 C6 175.2(3) . . . . ?
C5 C6 C7 N1 -178.9(3) . . . . ?
C5 C6 C7 C2 1.2(5) . . . . ?
C15 C10 C11 C12 -0.7(5) . . . . ?
N2 C10 C11 C12 -179.7(3) . . . . ?
C15 C10 C11 Cl1 179.8(3) . . . . ?
N2 C10 C11 Cl1 0.8(4) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
Cl1 C11 C12 C13 179.9(3) . . . . ?
C11 C12 C13 C14 0.3(5) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C10 0.1(5) . . . . ?
C11 C10 C15 C14 0.5(5) . . . . ?
N2 C10 C15 C14 179.5(3) . . . . ?
N2 C8 N1 C7 1.5(5) . . . . ?
C9 C8 N1 C7 -177.9(3) . . . . ?
C2 C7 N1 C8 4.4(5) . . . . ?
C6 C7 N1 C8 -175.5(3) . . . . ?
N1 C8 N2 C1 -7.2(5) . . . . ?
C9 C8 N2 C1 172.1(3) . . . . ?
N1 C8 N2 C10 171.4(3) . . . . ?
C9 C8 N2 C10 -9.2(4) . . . . ?
O1 C1 N2 C8 -175.4(3) . . . . ?
C2 C1 N2 C8 6.4(4) . . . . ?
O1 C1 N2 C10 5.9(4) . . . . ?
C2 C1 N2 C10 -172.3(3) . . . . ?
C15 C10 N2 C8 103.0(4) . . . . ?
C11 C10 N2 C8 -78.0(4) . . . . ?
C15 C10 N2 C1 -78.2(4) . . . . ?
C11 C10 N2 C1 100.8(4) . . . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_P21_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1897965'
loop_
_audit_author_name
_audit_author_address
'Osamu Kitagawa'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 I N2 O'
_chemical_formula_sum            'C15 H11 I N2 O'
_chemical_formula_weight         362.16

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   10.8013(2)
_cell_length_b                   15.1552(3)
_cell_length_c                   12.7524(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.8710(10)
_cell_angle_gamma                90
_cell_volume                     2079.98(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    100
_cell_measurement_reflns_used    256
_cell_measurement_theta_min      2.8907
_cell_measurement_theta_max      25.8878

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.173
_exptl_absorpt_coefficient_mu    2.302
_shelx_estimated_absorpt_T_min   0.639
_shelx_estimated_absorpt_T_max   0.691
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            23993
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.582
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             7181
_reflns_number_gt                7067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.957

_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       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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)+(0.0080P)²+0.2074P] 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 3197 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7181
_refine_ls_number_parameters     517
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0373
_refine_ls_wR_factor_gt          0.0369
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2186(4) 0.5204(3) 0.8303(3) 0.0134(9) Uani 1 1 d . . . . .
C2 C 0.3377(4) 0.4743(3) 0.8294(3) 0.0134(9) Uani 1 1 d . . . . .
C3 C 0.4343(4) 0.4913(3) 0.9068(4) 0.0175(10) Uani 1 1 d . . . . .
H3 H 0.421644 0.530737 0.962827 0.021 Uiso 1 1 calc R U . . .
C4 C 0.5471(4) 0.4511(3) 0.9019(4) 0.0217(11) Uani 1 1 d . . . . .
H4 H 0.611688 0.461095 0.955879 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5675(4) 0.3954(3) 0.8176(4) 0.0234(11) Uani 1 1 d . . . . .
H5 H 0.647393 0.370247 0.812803 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4730(4) 0.3768(3) 0.7417(4) 0.0223(11) Uani 1 1 d . . . . .
H6 H 0.487215 0.338269 0.685222 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3559(4) 0.4147(3) 0.7481(4) 0.0150(10) Uani 1 1 d . . . . .
C8 C 0.1523(4) 0.4279(3) 0.6783(3) 0.0149(10) Uani 1 1 d . . . . .
C9 C 0.0469(4) 0.4004(3) 0.6009(4) 0.0184(10) Uani 1 1 d . . . . .
H9A H 0.039924 0.441800 0.541658 0.028 Uiso 1 1 calc R U . . .
H9B H -0.030672 0.400460 0.635500 0.028 Uiso 1 1 calc R U . . .
H9C H 0.062731 0.340908 0.574942 0.028 Uiso 1 1 calc R U . . .
C10 C 0.0131(4) 0.5409(3) 0.7409(3) 0.0129(9) Uani 1 1 d . . . . .
C11 C -0.0104(4) 0.6046(3) 0.6630(3) 0.0144(9) Uani 1 1 d . . . . .
C12 C -0.1225(4) 0.6508(3) 0.6546(3) 0.0175(10) Uani 1 1 d . . . . .
H12 H -0.139087 0.693802 0.601118 0.021 Uiso 1 1 calc R U . . .
C13 C -0.2098(4) 0.6327(3) 0.7262(3) 0.0216(10) Uani 1 1 d . . . . .
H13 H -0.286222 0.664052 0.721673 0.026 Uiso 1 1 calc R U . . .
C14 C -0.1864(4) 0.5698(3) 0.8036(4) 0.0240(11) Uani 1 1 d . . . . .
H14 H -0.246619 0.557888 0.851870 0.029 Uiso 1 1 calc R U . . .
C15 C -0.0748(4) 0.5240(3) 0.8109(4) 0.0204(11) Uani 1 1 d . . . . .
H15 H -0.058836 0.480751 0.864258 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4381(4) 0.5887(3) 0.2483(3) 0.0141(9) Uani 1 1 d . . . . .
C17 C 0.3336(4) 0.6497(3) 0.2354(3) 0.0125(9) Uani 1 1 d . . . . .
C18 C 0.2770(4) 0.6695(3) 0.1350(3) 0.0155(10) Uani 1 1 d . . . . .
H18 H 0.307131 0.643092 0.074600 0.019 Uiso 1 1 calc R U . . .
C19 C 0.1781(4) 0.7269(3) 0.1237(3) 0.0179(10) Uani 1 1 d . . . . .
H19 H 0.139771 0.739835 0.055636 0.021 Uiso 1 1 calc R U . . .
C20 C 0.1338(4) 0.7663(3) 0.2130(4) 0.0193(10) Uani 1 1 d . . . . .
H20 H 0.066066 0.806425 0.204988 0.023 Uiso 1 1 calc R U . . .
C21 C 0.1877(4) 0.7473(3) 0.3115(4) 0.0192(10) Uani 1 1 d . . . . .
H21 H 0.156742 0.773951 0.371372 0.023 Uiso 1 1 calc R U . . .
C22 C 0.2888(4) 0.6885(3) 0.3245(3) 0.0142(9) Uani 1 1 d . . . . .
C23 C 0.4289(4) 0.6137(3) 0.4385(3) 0.0176(10) Uani 1 1 d . . . . .
C24 C 0.4822(5) 0.5902(3) 0.5473(3) 0.0245(11) Uani 1 1 d . . . . .
H24A H 0.438914 0.623370 0.599071 0.037 Uiso 1 1 calc R U . . .
H24B H 0.570834 0.604945 0.554950 0.037 Uiso 1 1 calc R U . . .
H24C H 0.471710 0.526788 0.558910 0.037 Uiso 1 1 calc R U . . .
C25 C 0.5880(4) 0.5165(3) 0.3748(3) 0.0151(10) Uani 1 1 d . . . . .
C26 C 0.7066(4) 0.5518(3) 0.3803(3) 0.0149(9) Uani 1 1 d . . . . .
C27 C 0.8087(4) 0.4970(3) 0.4026(3) 0.0173(10) Uani 1 1 d . . . . .
H27 H 0.890486 0.520654 0.407963 0.021 Uiso 1 1 calc R U . . .
C28 C 0.7900(4) 0.4077(3) 0.4168(3) 0.0190(10) Uani 1 1 d . . . . .
H28 H 0.859689 0.370115 0.431489 0.023 Uiso 1 1 calc R U . . .
C29 C 0.6719(4) 0.3722(3) 0.4102(4) 0.0213(11) Uani 1 1 d . . . . .
H29 H 0.660609 0.310664 0.420220 0.026 Uiso 1 1 calc R U . . .
C30 C 0.5699(4) 0.4268(3) 0.3888(4) 0.0200(10) Uani 1 1 d . . . . .
H30 H 0.488294 0.402979 0.383692 0.024 Uiso 1 1 calc R U . . .
C31 C 0.1525(4) 0.3644(3) 0.0324(3) 0.0144(9) Uani 1 1 d . . . . .
C32 C 0.2730(4) 0.3213(3) 0.0475(3) 0.0151(9) Uani 1 1 d . . . . .
C33 C 0.3203(4) 0.2753(3) -0.0350(3) 0.0178(10) Uani 1 1 d . . . . .
H33 H 0.273176 0.272015 -0.101232 0.021 Uiso 1 1 calc R U . . .
C34 C 0.4341(4) 0.2348(3) -0.0214(4) 0.0225(11) Uani 1 1 d . . . . .
H34 H 0.465105 0.202667 -0.077532 0.027 Uiso 1 1 calc R U . . .
C35 C 0.5045(4) 0.2412(3) 0.0765(4) 0.0251(11) Uani 1 1 d . . . . .
H35 H 0.583853 0.213887 0.085910 0.030 Uiso 1 1 calc R U . . .
C36 C 0.4596(4) 0.2866(3) 0.1584(4) 0.0215(10) Uani 1 1 d . . . . .
H36 H 0.507960 0.290480 0.223986 0.026 Uiso 1 1 calc R U . . .
C37 C 0.3423(4) 0.3272(3) 0.1455(3) 0.0183(10) Uani 1 1 d . . . . .
C38 C 0.1919(4) 0.4089(3) 0.2169(4) 0.0185(10) Uani 1 1 d . . . . .
C39 C 0.1414(4) 0.4562(4) 0.3083(4) 0.0277(12) Uani 1 1 d . . . . .
H39A H 0.202322 0.453240 0.369664 0.041 Uiso 1 1 calc R U . . .
H39B H 0.063890 0.427977 0.325095 0.041 Uiso 1 1 calc R U . . .
H39C H 0.125224 0.518064 0.289420 0.041 Uiso 1 1 calc R U . . .
C40 C -0.0002(4) 0.4552(3) 0.1132(3) 0.0167(10) Uani 1 1 d . . . . .
C41 C -0.1093(4) 0.4139(3) 0.1381(3) 0.0149(9) Uani 1 1 d . . . . .
C42 C -0.2190(4) 0.4625(3) 0.1352(3) 0.0171(10) Uani 1 1 d . . . . .
H42 H -0.294024 0.435287 0.151908 0.021 Uiso 1 1 calc R U . . .
C43 C -0.2179(4) 0.5510(3) 0.1077(4) 0.0196(11) Uani 1 1 d . . . . .
H43 H -0.292119 0.584610 0.107731 0.023 Uiso 1 1 calc R U . . .
C44 C -0.1105(5) 0.5911(3) 0.0802(4) 0.0233(11) Uani 1 1 d . . . . .
H44 H -0.111407 0.651393 0.059830 0.028 Uiso 1 1 calc R U . . .
C45 C -0.0018(4) 0.5429(3) 0.0824(4) 0.0198(10) Uani 1 1 d . . . . .
H45 H 0.072171 0.569944 0.062787 0.024 Uiso 1 1 calc R U . . .
I1 I 0.12678(3) 0.63738(2) 0.56179(2) 0.01574(7) Uani 1 1 d . . . . .
I2 I 0.73147(3) 0.68813(2) 0.35974(2) 0.01940(7) Uani 1 1 d . . . . .
I3 I -0.11044(3) 0.28013(2) 0.17588(2) 0.01934(7) Uani 1 1 d . . . . .
N1 N 0.2592(3) 0.3897(2) 0.6748(3) 0.0174(8) Uani 1 1 d . . . . .
N2 N 0.1296(3) 0.4935(2) 0.7497(3) 0.0141(8) Uani 1 1 d . . . . .
N3 N 0.3382(3) 0.6693(2) 0.4266(3) 0.0170(8) Uani 1 1 d . . . . .
N4 N 0.4804(3) 0.5729(2) 0.3549(3) 0.0128(8) Uani 1 1 d . . . . .
N5 N 0.2986(3) 0.3712(3) 0.2313(3) 0.0208(9) Uani 1 1 d . . . . .
N6 N 0.1175(3) 0.4087(2) 0.1221(3) 0.0145(8) Uani 1 1 d . . . . .
O1 O 0.1958(3) 0.5778(2) 0.8924(2) 0.0196(7) Uani 1 1 d . . . . .
O2 O 0.4885(3) 0.5533(2) 0.1778(2) 0.0184(7) Uani 1 1 d . . . . .
O3 O 0.0838(3) 0.3642(2) -0.0490(2) 0.0178(7) 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 O1 1.215(5) . ?
C1 N2 1.407(5) . ?
C1 C2 1.465(6) . ?
C2 C3 1.398(6) . ?
C2 C7 1.401(6) . ?
C3 C4 1.368(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(6) . ?
C6 H6 0.9500 . ?
C7 N1 1.394(6) . ?
C8 N1 1.295(6) . ?
C8 N2 1.384(6) . ?
C8 C9 1.501(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.381(6) . ?
C10 C11 1.393(6) . ?
C10 N2 1.445(5) . ?
C11 C12 1.395(6) . ?
C11 I1 2.105(4) . ?
C12 C13 1.394(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O2 1.215(5) . ?
C16 N4 1.418(5) . ?
C16 C17 1.458(6) . ?
C17 C22 1.402(6) . ?
C17 C18 1.402(6) . ?
C18 C19 1.376(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.405(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.369(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.409(6) . ?
C21 H21 0.9500 . ?
C22 N3 1.395(5) . ?
C23 N3 1.291(5) . ?
C23 N4 1.389(5) . ?
C23 C24 1.499(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.385(6) . ?
C25 C30 1.387(6) . ?
C25 N4 1.448(5) . ?
C26 C27 1.391(6) . ?
C26 I2 2.102(4) . ?
C27 C28 1.383(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.380(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(6) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 O3 1.223(5) . ?
C31 N6 1.406(6) . ?
C31 C32 1.454(6) . ?
C32 C33 1.394(6) . ?
C32 C37 1.404(6) . ?
C33 C34 1.372(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.409(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.373(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.406(6) . ?
C36 H36 0.9500 . ?
C37 N5 1.397(6) . ?
C38 N5 1.286(6) . ?
C38 N6 1.393(6) . ?
C38 C39 1.508(6) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C45 1.386(7) . ?
C40 C41 1.394(6) . ?
C40 N6 1.449(6) . ?
C41 C42 1.394(6) . ?
C41 I3 2.084(4) . ?
C42 C43 1.386(7) . ?
C42 H42 0.9500 . ?
C43 C44 1.380(7) . ?
C43 H43 0.9500 . ?
C44 C45 1.381(6) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 121.3(4) . . ?
O1 C1 C2 125.0(4) . . ?
N2 C1 C2 113.8(4) . . ?
C3 C2 C7 119.9(4) . . ?
C3 C2 C1 120.7(4) . . ?
C7 C2 C1 119.4(4) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N1 C7 C6 118.7(4) . . ?
N1 C7 C2 121.8(4) . . ?
C6 C7 C2 119.5(4) . . ?
N1 C8 N2 123.5(4) . . ?
N1 C8 C9 118.8(4) . . ?
N2 C8 C9 117.7(4) . . ?
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 . . ?
C15 C10 C11 119.7(4) . . ?
C15 C10 N2 120.0(4) . . ?
C11 C10 N2 120.3(4) . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 I1 120.4(3) . . ?
C12 C11 I1 119.1(3) . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.3(4) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O2 C16 N4 120.5(4) . . ?
O2 C16 C17 126.0(4) . . ?
N4 C16 C17 113.5(4) . . ?
C22 C17 C18 119.8(4) . . ?
C22 C17 C16 119.4(4) . . ?
C18 C17 C16 120.8(4) . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.9(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
N3 C22 C17 122.6(4) . . ?
N3 C22 C21 118.3(4) . . ?
C17 C22 C21 119.1(4) . . ?
N3 C23 N4 123.3(4) . . ?
N3 C23 C24 119.5(4) . . ?
N4 C23 C24 117.1(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 120.8(4) . . ?
C26 C25 N4 120.4(4) . . ?
C30 C25 N4 118.8(4) . . ?
C25 C26 C27 119.6(4) . . ?
C25 C26 I2 120.1(3) . . ?
C27 C26 I2 120.3(3) . . ?
C28 C27 C26 119.3(4) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C29 C28 C27 121.3(4) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 119.6(4) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C25 C30 C29 119.5(4) . . ?
C25 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
O3 C31 N6 120.4(4) . . ?
O3 C31 C32 125.7(4) . . ?
N6 C31 C32 113.9(4) . . ?
C33 C32 C37 120.1(4) . . ?
C33 C32 C31 120.4(4) . . ?
C37 C32 C31 119.6(4) . . ?
C34 C33 C32 120.7(4) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.4(4) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C36 C35 C34 120.6(4) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 120.3(4) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
N5 C37 C32 122.5(4) . . ?
N5 C37 C36 118.6(4) . . ?
C32 C37 C36 118.9(4) . . ?
N5 C38 N6 124.5(4) . . ?
N5 C38 C39 118.6(4) . . ?
N6 C38 C39 116.9(4) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C45 C40 C41 120.3(4) . . ?
C45 C40 N6 118.6(4) . . ?
C41 C40 N6 121.1(4) . . ?
C42 C41 C40 119.3(4) . . ?
C42 C41 I3 119.9(3) . . ?
C40 C41 I3 120.7(3) . . ?
C43 C42 C41 119.5(4) . . ?
C43 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
C44 C43 C42 121.0(4) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C45 119.6(4) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C44 C45 C40 120.2(4) . . ?
C44 C45 H45 119.9 . . ?
C40 C45 H45 119.9 . . ?
C8 N1 C7 118.4(4) . . ?
C8 N2 C1 122.7(4) . . ?
C8 N2 C10 120.6(3) . . ?
C1 N2 C10 116.7(4) . . ?
C23 N3 C22 118.2(4) . . ?
C23 N4 C16 122.9(4) . . ?
C23 N4 C25 119.8(3) . . ?
C16 N4 C25 117.1(3) . . ?
C38 N5 C37 117.3(4) . . ?
C38 N6 C31 122.1(4) . . ?
C38 N6 C40 120.3(4) . . ?
C31 N6 C40 117.6(4) . . ?

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
O1 C1 C2 C3 3.4(7) . . . . ?
N2 C1 C2 C3 -177.7(4) . . . . ?
O1 C1 C2 C7 -174.5(4) . . . . ?
N2 C1 C2 C7 4.4(6) . . . . ?
C7 C2 C3 C4 1.3(7) . . . . ?
C1 C2 C3 C4 -176.6(4) . . . . ?
C2 C3 C4 C5 2.2(7) . . . . ?
C3 C4 C5 C6 -3.3(7) . . . . ?
C4 C5 C6 C7 0.8(7) . . . . ?
C5 C6 C7 N1 -175.2(4) . . . . ?
C5 C6 C7 C2 2.7(7) . . . . ?
C3 C2 C7 N1 174.1(4) . . . . ?
C1 C2 C7 N1 -7.9(6) . . . . ?
C3 C2 C7 C6 -3.8(6) . . . . ?
C1 C2 C7 C6 174.2(4) . . . . ?
C15 C10 C11 C12 -0.5(6) . . . . ?
N2 C10 C11 C12 -179.7(4) . . . . ?
C15 C10 C11 I1 176.0(3) . . . . ?
N2 C10 C11 I1 -3.2(5) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
I1 C11 C12 C13 -175.9(3) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C11 C10 C15 C14 0.2(7) . . . . ?
N2 C10 C15 C14 179.4(4) . . . . ?
C13 C14 C15 C10 -0.1(7) . . . . ?
O2 C16 C17 C22 -177.2(4) . . . . ?
N4 C16 C17 C22 2.3(5) . . . . ?
O2 C16 C17 C18 3.4(7) . . . . ?
N4 C16 C17 C18 -177.1(4) . . . . ?
C22 C17 C18 C19 0.2(6) . . . . ?
C16 C17 C18 C19 179.7(4) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C18 C19 C20 C21 -0.7(7) . . . . ?
C19 C20 C21 C22 0.5(7) . . . . ?
C18 C17 C22 N3 177.7(4) . . . . ?
C16 C17 C22 N3 -1.8(6) . . . . ?
C18 C17 C22 C21 -0.4(6) . . . . ?
C16 C17 C22 C21 -179.9(4) . . . . ?
C20 C21 C22 N3 -178.1(4) . . . . ?
C20 C21 C22 C17 0.1(7) . . . . ?
C30 C25 C26 C27 -1.5(7) . . . . ?
N4 C25 C26 C27 178.1(4) . . . . ?
C30 C25 C26 I2 -179.6(3) . . . . ?
N4 C25 C26 I2 -0.1(6) . . . . ?
C25 C26 C27 C28 1.2(6) . . . . ?
I2 C26 C27 C28 179.4(3) . . . . ?
C26 C27 C28 C29 -0.5(7) . . . . ?
C27 C28 C29 C30 0.0(7) . . . . ?
C26 C25 C30 C29 1.0(7) . . . . ?
N4 C25 C30 C29 -178.5(4) . . . . ?
C28 C29 C30 C25 -0.3(7) . . . . ?
O3 C31 C32 C33 0.6(7) . . . . ?
N6 C31 C32 C33 -179.6(4) . . . . ?
O3 C31 C32 C37 179.8(4) . . . . ?
N6 C31 C32 C37 -0.3(6) . . . . ?
C37 C32 C33 C34 0.6(7) . . . . ?
C31 C32 C33 C34 179.8(4) . . . . ?
C32 C33 C34 C35 -1.1(7) . . . . ?
C33 C34 C35 C36 0.8(7) . . . . ?
C34 C35 C36 C37 0.1(7) . . . . ?
C33 C32 C37 N5 -179.0(4) . . . . ?
C31 C32 C37 N5 1.8(6) . . . . ?
C33 C32 C37 C36 0.3(7) . . . . ?
C31 C32 C37 C36 -178.9(4) . . . . ?
C35 C36 C37 N5 178.7(4) . . . . ?
C35 C36 C37 C32 -0.6(7) . . . . ?
C45 C40 C41 C42 -2.2(7) . . . . ?
N6 C40 C41 C42 175.8(4) . . . . ?
C45 C40 C41 I3 176.4(3) . . . . ?
N6 C40 C41 I3 -5.6(6) . . . . ?
C40 C41 C42 C43 0.0(7) . . . . ?
I3 C41 C42 C43 -178.6(3) . . . . ?
C41 C42 C43 C44 1.9(7) . . . . ?
C42 C43 C44 C45 -1.5(7) . . . . ?
C43 C44 C45 C40 -0.7(7) . . . . ?
C41 C40 C45 C44 2.6(7) . . . . ?
N6 C40 C45 C44 -175.5(4) . . . . ?
N2 C8 N1 C7 1.2(7) . . . . ?
C9 C8 N1 C7 -179.0(4) . . . . ?
C6 C7 N1 C8 -177.0(4) . . . . ?
C2 C7 N1 C8 5.1(6) . . . . ?
N1 C8 N2 C1 -4.7(6) . . . . ?
C9 C8 N2 C1 175.6(4) . . . . ?
N1 C8 N2 C10 172.3(4) . . . . ?
C9 C8 N2 C10 -7.5(6) . . . . ?
O1 C1 N2 C8 -179.5(4) . . . . ?
C2 C1 N2 C8 1.6(6) . . . . ?
O1 C1 N2 C10 3.5(6) . . . . ?
C2 C1 N2 C10 -175.4(3) . . . . ?
C15 C10 N2 C8 106.1(5) . . . . ?
C11 C10 N2 C8 -74.6(5) . . . . ?
C15 C10 N2 C1 -76.8(5) . . . . ?
C11 C10 N2 C1 102.5(5) . . . . ?
N4 C23 N3 C22 0.6(6) . . . . ?
C24 C23 N3 C22 -178.7(4) . . . . ?
C17 C22 N3 C23 0.2(6) . . . . ?
C21 C22 N3 C23 178.4(4) . . . . ?
N3 C23 N4 C16 0.2(6) . . . . ?
C24 C23 N4 C16 179.5(4) . . . . ?
N3 C23 N4 C25 175.4(4) . . . . ?
C24 C23 N4 C25 -5.3(6) . . . . ?
O2 C16 N4 C23 177.9(4) . . . . ?
C17 C16 N4 C23 -1.6(5) . . . . ?
O2 C16 N4 C25 2.5(6) . . . . ?
C17 C16 N4 C25 -177.0(3) . . . . ?
C26 C25 N4 C23 -87.4(5) . . . . ?
C30 C25 N4 C23 92.2(5) . . . . ?
C26 C25 N4 C16 88.1(5) . . . . ?
C30 C25 N4 C16 -92.3(5) . . . . ?
N6 C38 N5 C37 0.1(7) . . . . ?
C39 C38 N5 C37 179.4(4) . . . . ?
C32 C37 N5 C38 -1.7(6) . . . . ?
C36 C37 N5 C38 179.0(4) . . . . ?
N5 C38 N6 C31 1.4(7) . . . . ?
C39 C38 N6 C31 -177.9(4) . . . . ?
N5 C38 N6 C40 -178.4(4) . . . . ?
C39 C38 N6 C40 2.3(6) . . . . ?
O3 C31 N6 C38 178.7(4) . . . . ?
C32 C31 N6 C38 -1.2(6) . . . . ?
O3 C31 N6 C40 -1.5(6) . . . . ?
C32 C31 N6 C40 178.6(4) . . . . ?
C45 C40 N6 C38 89.6(5) . . . . ?
C41 C40 N6 C38 -88.5(5) . . . . ?
C45 C40 N6 C31 -90.2(5) . . . . ?
C41 C40 N6 C31 91.7(5) . . . . ?

_refine_diff_density_max         0.714
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_P21c_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1897964'
loop_
_audit_author_name
_audit_author_address
'Osamu Kitagawa'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 F N2 O'
_chemical_formula_sum            'C15 H11 F N2 O'
_chemical_formula_weight         254.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.4513(3)
_cell_length_b                   7.9032(3)
_cell_length_c                   23.1654(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.1070(10)
_cell_angle_gamma                90
_cell_volume                     1174.41(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    7370
_cell_measurement_theta_min      2.7247
_cell_measurement_theta_max      25.0768

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.780
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.322
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.97

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            12721
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.725
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2074
_reflns_number_gt                1880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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)+(0.0342P)²+0.7468P] 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_number_reflns         2074
_refine_ls_number_parameters     213
_refine_ls_number_restraints     304
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.049
_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 0.5421(2) 0.20889(19) 0.41344(6) 0.0182(3) Uani 1 1 d . U . . .
C2 C 0.5870(2) 0.2047(2) 0.47656(6) 0.0188(3) Uani 1 1 d . U . . .
C3 C 0.7718(2) 0.1335(2) 0.50240(7) 0.0225(4) Uani 1 1 d . U . . .
H3 H 0.872231 0.091272 0.478926 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8086(3) 0.1245(2) 0.56218(7) 0.0253(4) Uani 1 1 d . U . . .
H4 H 0.934554 0.076186 0.579862 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6601(3) 0.1866(2) 0.59661(7) 0.0247(4) Uani 1 1 d . U . . .
H5 H 0.684480 0.178195 0.637678 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4793(3) 0.2596(2) 0.57153(7) 0.0225(4) Uani 1 1 d . U . . .
H6 H 0.380402 0.302575 0.595375 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4397(2) 0.2711(2) 0.51080(6) 0.0188(3) Uani 1 1 d . U . . .
C8 C 0.2201(2) 0.3573(2) 0.43166(6) 0.0185(3) Uani 1 1 d . U . . .
C9 C 0.0270(2) 0.4444(2) 0.40560(7) 0.0232(4) Uani 1 1 d . U . . .
H9A H -0.069093 0.360808 0.386356 0.035 Uiso 1 1 calc R U . . .
H9B H 0.063441 0.527955 0.377100 0.035 Uiso 1 1 calc R U . . .
H9C H -0.040074 0.501524 0.436238 0.035 Uiso 1 1 calc R U . . .
C10A C 0.323(3) 0.3207(19) 0.3333(6) 0.020(2) Uani 0.204(3) 1 d G U P A 1
C11A C 0.175(2) 0.217(2) 0.3030(7) 0.019(2) Uani 0.204(3) 1 d G U P A 1
C12A C 0.1347(19) 0.2321(19) 0.2431(7) 0.020(2) Uani 0.204(3) 1 d G U P A 1
H12A H 0.033242 0.161462 0.222380 0.024 Uiso 0.204(3) 1 calc R U P A 1
C13A C 0.243(2) 0.3500(17) 0.2134(6) 0.019(2) Uani 0.204(3) 1 d G U P A 1
H13A H 0.215650 0.359987 0.172423 0.023 Uiso 0.204(3) 1 calc R U P A 1
C14A C 0.391(2) 0.4533(14) 0.2437(6) 0.020(2) Uani 0.204(3) 1 d G U P A 1
H14A H 0.465510 0.533883 0.223377 0.024 Uiso 0.204(3) 1 calc R U P A 1
C15A C 0.432(3) 0.4387(16) 0.3036(6) 0.029(2) Uani 0.204(3) 1 d G U P A 1
H15A H 0.532964 0.509257 0.324290 0.034 Uiso 0.204(3) 1 calc R U P A 1
F1A F 0.0752(8) 0.1004(7) 0.3300(2) 0.0347(17) Uani 0.204(3) 1 d . U P A 1
C10 C 0.2968(6) 0.2938(4) 0.33105(14) 0.0170(8) Uani 0.796(3) 1 d G U P A 2
C11 C 0.4124(5) 0.3971(3) 0.29797(14) 0.0185(6) Uani 0.796(3) 1 d G U P A 2
C12 C 0.3614(5) 0.4078(3) 0.23826(14) 0.0220(8) Uani 0.796(3) 1 d G U P A 2
H12 H 0.440386 0.478368 0.215645 0.026 Uiso 0.796(3) 1 calc R U P A 2
C13 C 0.1947(5) 0.3151(4) 0.21163(14) 0.0251(8) Uani 0.796(3) 1 d G U P A 2
H13 H 0.159755 0.322397 0.170816 0.030 Uiso 0.796(3) 1 calc R U P A 2
C14 C 0.0790(4) 0.2118(5) 0.24471(18) 0.0259(7) Uani 0.796(3) 1 d G U P A 2
H14 H -0.034908 0.148483 0.226509 0.031 Uiso 0.796(3) 1 calc R U P A 2
C15 C 0.1301(5) 0.2011(5) 0.30442(17) 0.0235(7) Uani 0.796(3) 1 d G U P A 2
H15 H 0.051060 0.130539 0.327033 0.028 Uiso 0.796(3) 1 calc R U P A 2
F1 F 0.57185(18) 0.48597(15) 0.32398(5) 0.0254(4) Uani 0.796(3) 1 d . U P A 2
N1 N 0.2568(2) 0.34817(17) 0.48742(5) 0.0194(3) Uani 1 1 d . U . . .
N2 N 0.35377(19) 0.28937(16) 0.39365(5) 0.0179(3) Uani 1 1 d . U . . .
O1 O 0.65304(17) 0.14835(14) 0.37895(4) 0.0226(3) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2253(18) . ?
C1 N2 1.404(2) . ?
C1 C2 1.460(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.403(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(2) . ?
C6 H6 0.9500 . ?
C7 N1 1.386(2) . ?
C8 N1 1.290(2) . ?
C8 N2 1.4028(19) . ?
C8 C9 1.494(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10A C11A 1.3900 . ?
C10A C15A 1.3900 . ?
C10A N2 1.413(14) . ?
C11A F1A 1.321(12) . ?
C11A C12A 1.3900 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3900 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3900 . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C10 N2 1.458(3) . ?
C11 F1 1.335(3) . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 120.60(13) . . ?
O1 C1 C2 125.21(14) . . ?
N2 C1 C2 114.19(13) . . ?
C3 C2 C7 120.51(14) . . ?
C3 C2 C1 120.57(14) . . ?
C7 C2 C1 118.91(14) . . ?
C4 C3 C2 119.97(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.84(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.57(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.41(15) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N1 C7 C2 122.90(13) . . ?
N1 C7 C6 118.42(14) . . ?
C2 C7 C6 118.67(14) . . ?
N1 C8 N2 123.22(14) . . ?
N1 C8 C9 119.10(13) . . ?
N2 C8 C9 117.68(13) . . ?
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 . . ?
C11A C10A C15A 120.0 . . ?
C11A C10A N2 114.4(9) . . ?
C15A C10A N2 125.6(9) . . ?
F1A C11A C10A 121.1(10) . . ?
F1A C11A C12A 118.9(10) . . ?
C10A C11A C12A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C15A C14A C13A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C14A C15A C10A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C10A C15A H15A 120.0 . . ?
C11 C10 C15 120.0 . . ?
C11 C10 N2 118.0(2) . . ?
C15 C10 N2 122.0(2) . . ?
F1 C11 C12 120.5(2) . . ?
F1 C11 C10 119.5(2) . . ?
C12 C11 C10 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C8 N1 C7 118.25(13) . . ?
C8 N2 C1 122.44(12) . . ?
C8 N2 C10A 121.6(7) . . ?
C1 N2 C10A 115.3(7) . . ?
C8 N2 C10 120.55(18) . . ?
C1 N2 C10 116.96(18) . . ?

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
O1 C1 C2 C3 2.5(2) . . . . ?
N2 C1 C2 C3 -177.99(14) . . . . ?
O1 C1 C2 C7 -176.50(15) . . . . ?
N2 C1 C2 C7 3.0(2) . . . . ?
C7 C2 C3 C4 1.5(2) . . . . ?
C1 C2 C3 C4 -177.48(15) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C3 C2 C7 N1 177.86(14) . . . . ?
C1 C2 C7 N1 -3.1(2) . . . . ?
C3 C2 C7 C6 -2.0(2) . . . . ?
C1 C2 C7 C6 177.04(14) . . . . ?
C5 C6 C7 N1 -179.01(14) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C15A C10A C11A F1A 177.6(14) . . . . ?
N2 C10A C11A F1A -0.5(12) . . . . ?
C15A C10A C11A C12A 0.0 . . . . ?
N2 C10A C11A C12A -178.0(12) . . . . ?
F1A C11A C12A C13A -177.6(13) . . . . ?
C10A C11A C12A C13A 0.0 . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C13A C14A C15A C10A 0.0 . . . . ?
C11A C10A C15A C14A 0.0 . . . . ?
N2 C10A C15A C14A 177.8(13) . . . . ?
C15 C10 C11 F1 179.8(3) . . . . ?
N2 C10 C11 F1 1.0(3) . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
N2 C10 C11 C12 -178.8(3) . . . . ?
F1 C11 C12 C13 -179.8(3) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
N2 C10 C15 C14 178.8(3) . . . . ?
N2 C8 N1 C7 1.6(2) . . . . ?
C9 C8 N1 C7 -178.18(13) . . . . ?
C2 C7 N1 C8 0.7(2) . . . . ?
C6 C7 N1 C8 -179.43(14) . . . . ?
N1 C8 N2 C1 -1.5(2) . . . . ?
C9 C8 N2 C1 178.27(14) . . . . ?
N1 C8 N2 C10A -171.6(8) . . . . ?
C9 C8 N2 C10A 8.2(8) . . . . ?
N1 C8 N2 C10 175.86(19) . . . . ?
C9 C8 N2 C10 -4.3(2) . . . . ?
O1 C1 N2 C8 178.66(14) . . . . ?
C2 C1 N2 C8 -0.9(2) . . . . ?
O1 C1 N2 C10A -10.7(7) . . . . ?
C2 C1 N2 C10A 169.7(7) . . . . ?
O1 C1 N2 C10 1.2(2) . . . . ?
C2 C1 N2 C10 -178.37(18) . . . . ?
C11A C10A N2 C8 -81.8(8) . . . . ?
C15A C10A N2 C8 100.3(9) . . . . ?
C11A C10A N2 C1 107.5(8) . . . . ?
C15A C10A N2 C1 -70.4(11) . . . . ?
C11 C10 N2 C8 112.0(2) . . . . ?
C15 C10 N2 C8 -66.8(2) . . . . ?
C11 C10 N2 C1 -70.5(3) . . . . ?
C15 C10 N2 C1 110.7(2) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_st180709a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1897966'
loop_
_audit_author_name
_audit_author_address
'Osamu Kitagawa'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 I N2 O'
_chemical_formula_sum            'C15 H11 I N2 O'
_chemical_formula_weight         362.16

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

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

_cell_length_a                   15.8947(3)
_cell_length_b                   21.2266(4)
_cell_length_c                   8.08590(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2728.11(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    321
_cell_measurement_theta_min      5.0199
_cell_measurement_theta_max      26.7099

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.880
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.340
_shelx_estimated_absorpt_T_min   0.233
_shelx_estimated_absorpt_T_max   0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4376
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            15044
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.563
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_full        25.021
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2347
_reflns_number_gt                2318
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_max     0.940
_reflns_Friedel_fraction_full    0.940

_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       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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)+(0.0149P)²+2.2547P] 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 1011 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2347
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0136
_refine_ls_R_factor_gt           0.0134
_refine_ls_wR_factor_ref         0.0333
_refine_ls_wR_factor_gt          0.0332
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.30502(18) 0.37207(14) 0.4458(4) 0.0130(6) Uani 1 1 d . . . . .
C2 C 0.34039(19) 0.40055(15) 0.2973(4) 0.0130(6) Uani 1 1 d . . . . .
C3 C 0.42645(18) 0.39349(14) 0.2618(4) 0.0140(6) Uani 1 1 d . . . . .
H3 H 0.461646 0.370414 0.334972 0.017 Uiso 1 1 calc R U . . .
C4 C 0.4597(2) 0.42013(14) 0.1206(4) 0.0168(6) Uani 1 1 d . . . . .
H4 H 0.517973 0.415816 0.097106 0.020 Uiso 1 1 calc R U . . .
C5 C 0.40758(19) 0.45355(14) 0.0119(4) 0.0175(7) Uani 1 1 d . . . . .
H5 H 0.430528 0.471242 -0.086139 0.021 Uiso 1 1 calc R U . . .
C6 C 0.3232(2) 0.46092(14) 0.0463(4) 0.0165(6) Uani 1 1 d . . . . .
H6 H 0.288328 0.483678 -0.028064 0.020 Uiso 1 1 calc R U . . .
C7 C 0.28877(18) 0.43497(14) 0.1906(4) 0.0137(6) Uani 1 1 d . . . . .
C8 C 0.17214(17) 0.41936(12) 0.3535(6) 0.0157(6) Uani 1 1 d . . . . .
C9 C 0.08074(19) 0.42952(15) 0.3913(5) 0.0251(8) Uani 1 1 d . . . . .
H9A H 0.056002 0.457119 0.307167 0.038 Uiso 1 1 calc R U . . .
H9B H 0.075079 0.449182 0.500378 0.038 Uiso 1 1 calc R U . . .
H9C H 0.051431 0.388904 0.390967 0.038 Uiso 1 1 calc R U . . .
C10 C 0.17678(18) 0.35350(14) 0.6028(4) 0.0133(6) Uani 1 1 d . . . . .
C11 C 0.14101(18) 0.29387(15) 0.5864(4) 0.0154(7) Uani 1 1 d . . . . .
C12 C 0.0986(2) 0.26791(16) 0.7204(5) 0.0196(7) Uani 1 1 d . . . . .
H12 H 0.072057 0.228017 0.709618 0.023 Uiso 1 1 calc R U . . .
C13 C 0.09476(15) 0.29979(13) 0.8694(7) 0.0218(6) Uani 1 1 d . . . . .
H13 H 0.066577 0.281179 0.960755 0.026 Uiso 1 1 calc R U . . .
C14 C 0.13165(18) 0.35871(15) 0.8869(5) 0.0204(8) Uani 1 1 d . . . . .
H14 H 0.129147 0.380410 0.989537 0.024 Uiso 1 1 calc R U . . .
C15 C 0.1725(2) 0.38560(15) 0.7510(4) 0.0176(7) Uani 1 1 d . . . . .
H15 H 0.197473 0.426105 0.760763 0.021 Uiso 1 1 calc R U . . .
I1 I 0.15134(2) 0.24250(2) 0.36515(6) 0.01830(7) Uani 1 1 d . . . . .
N1 N 0.20332(15) 0.44512(12) 0.2222(3) 0.0150(5) Uani 1 1 d . . . . .
N2 N 0.21802(15) 0.38299(11) 0.4638(3) 0.0127(5) Uani 1 1 d . . . . .
O1 O 0.34393(12) 0.34161(11) 0.5475(3) 0.0184(5) 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 O1 1.215(4) . ?
C1 N2 1.410(4) . ?
C1 C2 1.457(4) . ?
C2 C7 1.397(4) . ?
C2 C3 1.406(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(4) . ?
C6 H6 0.9500 . ?
C7 N1 1.399(4) . ?
C8 N1 1.293(5) . ?
C8 N2 1.386(5) . ?
C8 C9 1.500(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.380(5) . ?
C10 C11 1.394(4) . ?
C10 N2 1.444(4) . ?
C11 C12 1.391(5) . ?
C11 I1 2.101(3) . ?
C12 C13 1.383(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 121.1(3) . . ?
O1 C1 C2 125.6(3) . . ?
N2 C1 C2 113.3(3) . . ?
C7 C2 C3 120.1(3) . . ?
C7 C2 C1 120.0(3) . . ?
C3 C2 C1 120.0(3) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 N1 122.5(3) . . ?
C2 C7 C6 119.4(3) . . ?
N1 C7 C6 118.1(3) . . ?
N1 C8 N2 124.2(3) . . ?
N1 C8 C9 118.5(3) . . ?
N2 C8 C9 117.3(4) . . ?
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 . . ?
C15 C10 C11 120.8(3) . . ?
C15 C10 N2 119.0(3) . . ?
C11 C10 N2 120.3(3) . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 I1 119.7(2) . . ?
C10 C11 I1 121.4(2) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 118.9(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 120.2(3) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C8 N1 C7 117.2(3) . . ?
C8 N2 C1 122.8(3) . . ?
C8 N2 C10 120.2(3) . . ?
C1 N2 C10 117.0(2) . . ?

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
O1 C1 C2 C7 -179.5(3) . . . . ?
N2 C1 C2 C7 0.5(4) . . . . ?
O1 C1 C2 C3 0.3(5) . . . . ?
N2 C1 C2 C3 -179.7(3) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 C4 179.6(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C3 C2 C7 N1 -178.0(3) . . . . ?
C1 C2 C7 N1 1.8(4) . . . . ?
C3 C2 C7 C6 1.6(4) . . . . ?
C1 C2 C7 C6 -178.6(3) . . . . ?
C5 C6 C7 C2 -1.2(5) . . . . ?
C5 C6 C7 N1 178.4(3) . . . . ?
C15 C10 C11 C12 1.9(5) . . . . ?
N2 C10 C11 C12 -177.2(3) . . . . ?
C15 C10 C11 I1 -177.3(2) . . . . ?
N2 C10 C11 I1 3.5(4) . . . . ?
C10 C11 C12 C13 -2.4(5) . . . . ?
I1 C11 C12 C13 176.8(2) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C11 C10 C15 C14 -0.4(5) . . . . ?
N2 C10 C15 C14 178.8(3) . . . . ?
C13 C14 C15 C10 -0.8(5) . . . . ?
N2 C8 N1 C7 0.3(5) . . . . ?
C9 C8 N1 C7 179.8(3) . . . . ?
C2 C7 N1 C8 -2.3(4) . . . . ?
C6 C7 N1 C8 178.2(3) . . . . ?
N1 C8 N2 C1 2.1(5) . . . . ?
C9 C8 N2 C1 -177.4(3) . . . . ?
N1 C8 N2 C10 -176.9(3) . . . . ?
C9 C8 N2 C10 3.6(4) . . . . ?
O1 C1 N2 C8 177.6(3) . . . . ?
C2 C1 N2 C8 -2.4(4) . . . . ?
O1 C1 N2 C10 -3.3(4) . . . . ?
C2 C1 N2 C10 176.7(2) . . . . ?
C15 C10 N2 C8 -91.0(4) . . . . ?
C11 C10 N2 C8 88.2(4) . . . . ?
C15 C10 N2 C1 89.9(3) . . . . ?
C11 C10 N2 C1 -90.9(3) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.068

