# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_2a
_database_code_depnum_ccdc_archive 'CCDC 2254119'
loop_
_audit_author_name
_audit_author_address
'Takahiro Tsuchiya'
;Kitasato University
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H13 N)'
_chemical_formula_sum            'C34 H26 N2'
_chemical_formula_weight         462.57
_chemical_melting_point          510-512
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0145(2)
_cell_length_b                   10.9285(2)
_cell_length_c                   12.2912(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.106(2)
_cell_angle_gamma                90
_cell_volume                     1207.76(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5118
_cell_measurement_temperature    120
_cell_measurement_theta_max      74.2810
_cell_measurement_theta_min      5.4350
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.044
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.878
_diffrn_reflns_theta_min         5.422
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2366
_reflns_number_total             2501
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.4291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C7 \\sim C8 \\sim C9 \\sim C10:
within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.05 and sigma for terminal
atoms of 0.1
3. Others
 Fixed Sof: C1(0.5) C2(0.5) H2(0.5) C3(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5)
 C6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) C10(0.5) H10(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17574(10) 0.81676(9) 0.61658(8) 0.0224(2) Uani 1 1 d . . . . .
C1 C 0.1149(12) 0.7139(14) 0.5772(10) 0.0176(16) Uani 0.5 1 d . U P A -1
C2 C 0.2042(18) 0.5948(13) 0.5647(16) 0.0194(16) Uani 0.5 1 d . U P A -1
H2 H 0.306(5) 0.595(3) 0.576(3) 0.023 Uiso 0.5 1 d R . P B -1
C3 C 0.0984(3) 0.5142(2) 0.51994(17) 0.0174(4) Uani 0.5 1 d . U P A -1
C4 C 0.1335(3) 0.3937(2) 0.49378(18) 0.0192(4) Uani 0.5 1 d . U P A -1
H4 H 0.244(3) 0.375(3) 0.509(2) 0.023 Uiso 0.5 1 d R . P C -1
C5 C 0.0456(11) 0.2966(8) 0.4507(10) 0.0111(12) Uani 0.5 1 d . U P A -1
H5 H 0.091(4) 0.222(3) 0.453(3) 0.013 Uiso 0.5 1 d R . P D -1
C6 C -0.1170(13) 0.3022(13) 0.4223(10) 0.018(2) Uani 0.5 1 d . . P A -1
C7 C -0.2035(19) 0.3916(13) 0.4333(16) 0.0178(16) Uani 0.5 1 d . U P A -1
H7 H -0.308(4) 0.388(3) 0.395(2) 0.021 Uiso 0.5 1 d R . P E -1
C8 C -0.1828(3) 0.5164(2) 0.47095(17) 0.0184(4) Uani 0.5 1 d . U P A -1
H8 H -0.273(3) 0.570(3) 0.469(2) 0.022 Uiso 0.5 1 d R . P F -1
C9 C -0.0510(3) 0.5709(2) 0.51240(17) 0.0178(4) Uani 0.5 1 d . U P A -1
C10 C -0.0287(14) 0.6866(10) 0.5461(12) 0.0211(16) Uani 0.5 1 d . U P A -1
H10 H -0.113(5) 0.751(4) 0.560(3) 0.025 Uiso 0.5 1 d R . P G -1
C11 C 0.32971(12) 0.84544(10) 0.61321(9) 0.0203(2) Uani 1 1 d . . . . .
C12 C 0.40580(13) 0.82073(10) 0.52076(9) 0.0222(2) Uani 1 1 d . . . . .
H12 H 0.3531(16) 0.7836(13) 0.4563(12) 0.027 Uiso 1 1 d R . . . .
C13 C 0.55618(13) 0.84938(11) 0.52001(10) 0.0240(3) Uani 1 1 d . . . . .
H13 H 0.6084(16) 0.8348(13) 0.4533(13) 0.029 Uiso 1 1 d R . . . .
C14 C 0.63054(13) 0.90526(11) 0.60963(10) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.7358(17) 0.9253(14) 0.6090(12) 0.030 Uiso 1 1 d R . . . .
C15 C 0.55344(13) 0.93185(11) 0.70071(10) 0.0268(3) Uani 1 1 d . . . . .
H15 H 0.6039(17) 0.9721(14) 0.7625(13) 0.032 Uiso 1 1 d R . . . .
C16 C 0.40435(13) 0.90181(11) 0.70246(10) 0.0253(3) Uani 1 1 d . . . . .
H16 H 0.3522(17) 0.9181(14) 0.7673(13) 0.030 Uiso 1 1 d R . . . .
C17 C 0.08580(12) 0.90195(10) 0.67099(9) 0.0206(2) Uani 1 1 d . . . . .
C18 C 0.07644(13) 1.02273(11) 0.63547(10) 0.0245(3) Uani 1 1 d . . . . .
H18 H 0.1298(17) 1.0494(14) 0.5714(12) 0.029 Uiso 1 1 d R . . . .
C19 C -0.00785(13) 1.10700(11) 0.68873(10) 0.0272(3) Uani 1 1 d . . . . .
H19 H -0.0124(17) 1.1915(15) 0.6636(13) 0.033 Uiso 1 1 d R . . . .
C20 C -0.08207(13) 1.07126(12) 0.77880(10) 0.0269(3) Uani 1 1 d . . . . .
H20 H -0.1398(17) 1.1307(14) 0.8157(13) 0.032 Uiso 1 1 d R . . . .
C21 C -0.07244(13) 0.95105(12) 0.81429(10) 0.0268(3) Uani 1 1 d . . . . .
H21 H -0.1262(17) 0.9265(14) 0.8766(13) 0.032 Uiso 1 1 d R . . . .
C22 C 0.01070(12) 0.86556(11) 0.76063(9) 0.0238(3) Uani 1 1 d . . . . .
H22 H 0.0162(16) 0.7801(14) 0.7846(12) 0.029 Uiso 1 1 d 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
N1 C1 1.327(14) . ?
N1 C11 1.4263(14) . ?
N1 C17 1.4314(14) . ?
C1 C2 1.54(2) . ?
C1 C10 1.357(18) . ?
C2 H2 0.92(5) . ?
C2 C3 1.383(16) . ?
C3 C4 1.397(4) . ?
C3 C9 1.479(4) . ?
C4 H4 1.02(3) . ?
C4 C5 1.405(9) . ?
C5 H5 0.91(4) . ?
C5 C6 1.483(15) . ?
C6 C7 1.26(2) . ?
C7 H7 1.02(4) . ?
C7 C8 1.447(14) . ?
C8 H8 1.00(3) . ?
C8 C9 1.393(4) . ?
C9 C10 1.341(12) . ?
C10 H10 1.06(5) . ?
C11 C12 1.3950(16) . ?
C11 C16 1.3893(16) . ?
C12 H12 0.982(15) . ?
C12 C13 1.3919(16) . ?
C13 H13 0.987(16) . ?
C13 C14 1.3893(17) . ?
C14 H14 0.974(16) . ?
C14 C15 1.3899(18) . ?
C15 H15 0.963(16) . ?
C15 C16 1.3852(17) . ?
C16 H16 0.970(16) . ?
C17 C18 1.3910(16) . ?
C17 C22 1.3918(16) . ?
C18 H18 0.996(16) . ?
C18 C19 1.3875(17) . ?
C19 H19 0.974(16) . ?
C19 C20 1.3900(18) . ?
C20 H20 0.966(16) . ?
C20 C21 1.3850(18) . ?
C21 H21 0.973(16) . ?
C21 C22 1.3930(17) . ?
C22 H22 0.979(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 123.6(5) . . ?
C1 N1 C17 119.2(5) . . ?
C11 N1 C17 117.10(9) . . ?
N1 C1 C2 123.1(10) . . ?
N1 C1 C10 130.6(12) . . ?
C10 C1 C2 106.3(12) . . ?
C1 C2 H2 120(3) . . ?
C3 C2 C1 103.1(11) . . ?
C3 C2 H2 136(2) . . ?
C2 C3 C4 122.0(7) . . ?
C2 C3 C9 110.9(7) . . ?
C4 C3 C9 126.9(2) . . ?
C3 C4 H4 112.6(18) . . ?
C3 C4 C5 131.9(5) . . ?
C5 C4 H4 115.5(18) . . ?
C4 C5 H5 115(2) . . ?
C4 C5 C6 125.4(9) . . ?
C6 C5 H5 118(2) . . ?
C7 C6 C5 127.8(13) . . ?
C6 C7 H7 118(2) . . ?
C6 C7 C8 134.2(14) . . ?
C8 C7 H7 106(2) . . ?
C7 C8 H8 117.3(19) . . ?
C9 C8 C7 127.4(7) . . ?
C9 C8 H8 115.3(17) . . ?
C8 C9 C3 126.3(2) . . ?
C10 C9 C3 105.1(6) . . ?
C10 C9 C8 128.4(6) . . ?
C1 C10 H10 119(2) . . ?
C9 C10 C1 114.4(10) . . ?
C9 C10 H10 126(2) . . ?
C12 C11 N1 121.16(10) . . ?
C16 C11 N1 119.45(10) . . ?
C16 C11 C12 119.37(10) . . ?
C11 C12 H12 120.0(9) . . ?
C13 C12 C11 119.85(11) . . ?
C13 C12 H12 120.2(9) . . ?
C12 C13 H13 119.4(9) . . ?
C14 C13 C12 120.56(11) . . ?
C14 C13 H13 119.9(9) . . ?
C13 C14 H14 120.5(9) . . ?
C13 C14 C15 119.33(11) . . ?
C15 C14 H14 120.2(9) . . ?
C14 C15 H15 119.7(9) . . ?
C16 C15 C14 120.30(11) . . ?
C16 C15 H15 120.0(9) . . ?
C11 C16 H16 119.6(9) . . ?
C15 C16 C11 120.56(11) . . ?
C15 C16 H16 119.8(9) . . ?
C18 C17 N1 119.62(10) . . ?
C18 C17 C22 119.84(10) . . ?
C22 C17 N1 120.52(10) . . ?
C17 C18 H18 120.3(9) . . ?
C19 C18 C17 120.31(11) . . ?
C19 C18 H18 119.4(9) . . ?
C18 C19 H19 119.5(9) . . ?
C18 C19 C20 120.02(11) . . ?
C20 C19 H19 120.5(9) . . ?
C19 C20 H20 119.4(9) . . ?
C21 C20 C19 119.64(11) . . ?
C21 C20 H20 120.9(9) . . ?
C20 C21 H21 119.1(9) . . ?
C20 C21 C22 120.71(11) . . ?
C22 C21 H21 120.2(9) . . ?
C17 C22 C21 119.46(11) . . ?
C17 C22 H22 119.6(9) . . ?
C21 C22 H22 120.9(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 2254124'
loop_
_audit_author_name
_audit_author_address
'Takahiro Tsuchiya'
;Kitasato University
Japan
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            2,6-[(p-MeOBz)2N]2-azulene
_chemical_name_systematic        
N2,N2,N6,N6-tetrakis(4-methoxyphenyl)azulene-2,6-diamine
_chemical_formula_moiety         '2(C19 H17 N O2)'
_chemical_formula_sum            'C38 H34 N2 O4'
_chemical_formula_weight         582.67
_chemical_melting_point          505-508
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3794(3)
_cell_length_b                   9.6787(2)
_cell_length_c                   14.2709(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.337(3)
_cell_angle_gamma                90
_cell_volume                     1500.36(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4736
_cell_measurement_temperature    120
_cell_measurement_theta_max      73.9920
_cell_measurement_theta_min      4.0520
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.351
_exptl_crystal_size_min          0.198
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8354
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.428
_diffrn_reflns_theta_min         4.070
_diffrn_ambient_temperature      120
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2760
_reflns_number_total             2935
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0193P)²+1.3978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C7 \\sim C8 \\sim C9 \\sim C10:
within 2A with sigma of 0.0001 and sigma for terminal atoms of 0.01
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.0001 and sigma for terminal
atoms of 0.1
3. Others
 Fixed Sof: C1(0.5) C6(0.5) C2(0.5) H2(0.5) C3(0.5) C4(0.5) H4(0.5) C5(0.5)
 H5(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) C10(0.5) H10(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C19(H19),
 C20(H20), C22(H22), C23(H23)
4.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4827(14) 0.2505(13) 0.4078(10) 0.0268(3) Uani 0.5 1 d . U P A -1
C6 C 0.5178(13) 0.7296(9) 0.5903(10) 0.0291(17) Uani 0.5 1 d . . P A -1
C2 C 0.5742(5) 0.3034(5) 0.4876(4) 0.0268(3) Uani 0.5 1 d . U P A -1
H2 H 0.647051 0.253961 0.520216 0.032 Uiso 0.5 1 calc R . P A -1
C3 C 0.5489(4) 0.4364(4) 0.5152(3) 0.0268(3) Uani 0.5 1 d . U P A -1
C4 C 0.6212(4) 0.5140(4) 0.5933(3) 0.0268(3) Uani 0.5 1 d . U P A -1
H4 H 0.692492 0.467894 0.632815 0.032 Uiso 0.5 1 calc R . P A -1
C5 C 0.6060(7) 0.6494(5) 0.6234(5) 0.0268(3) Uani 0.5 1 d . U P A -1
H5 H 0.676(4) 0.677(4) 0.680(3) 0.021(10) Uiso 0.5 1 d . . P B -1
C7 C 0.4132(5) 0.7258(5) 0.4994(4) 0.0268(3) Uani 0.5 1 d . U P A -1
H7 H 0.359(4) 0.810(5) 0.480(3) 0.025(11) Uiso 0.5 1 d . . P C -1
C8 C 0.3767(4) 0.6105(4) 0.4397(3) 0.0268(3) Uani 0.5 1 d . U P A -1
H8 H 0.293(4) 0.623(4) 0.381(3) 0.018(10) Uiso 0.5 1 d . . P D -1
C9 C 0.4319(4) 0.4803(4) 0.4451(3) 0.0268(3) Uani 0.5 1 d . U P A -1
C10 C 0.3905(7) 0.3757(5) 0.3759(5) 0.0268(3) Uani 0.5 1 d . U P A -1
H10 H 0.319950 0.379186 0.319843 0.032 Uiso 0.5 1 calc R . P A -1
N1 N 0.47894(16) 0.13514(19) 0.35936(14) 0.0353(4) Uani 1 1 d . . . . .
C11 C 0.36714(19) 0.0807(2) 0.29665(16) 0.0310(5) Uani 1 1 d . . . . .
C12 C 0.2664(2) 0.0623(3) 0.33105(16) 0.0378(5) Uani 1 1 d . . . . .
H12 H 0.272762 0.086736 0.396860 0.045 Uiso 1 1 calc R . . . .
C13 C 0.1562(2) 0.0088(2) 0.27095(16) 0.0344(5) Uani 1 1 d . . . . .
H13 H 0.087756 -0.002912 0.295390 0.041 Uiso 1 1 calc R . . . .
C14 C 0.14719(19) -0.0273(2) 0.17522(15) 0.0305(4) Uani 1 1 d . . . . .
C15 C 0.24781(19) -0.0093(2) 0.14036(15) 0.0325(5) Uani 1 1 d . . . . .
H15 H 0.241457 -0.033881 0.074594 0.039 Uiso 1 1 calc R . . . .
C16 C 0.35702(19) 0.0440(2) 0.20021(16) 0.0303(4) Uani 1 1 d . . . . .
H16 H 0.425276 0.055679 0.175571 0.036 Uiso 1 1 calc R . . . .
O1 O 0.04391(14) -0.08194(18) 0.10963(11) 0.0408(4) Uani 1 1 d . . . . .
C17 C -0.0634(2) -0.0935(3) 0.1405(2) 0.0523(7) Uani 1 1 d . . . . .
H17A H -0.132088 -0.126372 0.085618 0.078 Uiso 1 1 calc GR . . . .
H17B H -0.083817 -0.002969 0.162055 0.078 Uiso 1 1 calc GR . . . .
H17C H -0.048209 -0.159301 0.194993 0.078 Uiso 1 1 calc GR . . . .
C18 C 0.59347(19) 0.0733(2) 0.35966(15) 0.0315(5) Uani 1 1 d . . . . .
C19 C 0.6233(2) -0.0603(2) 0.39254(16) 0.0333(5) Uani 1 1 d . . . . .
H19 H 0.564265 -0.115694 0.410129 0.040 Uiso 1 1 calc R . . . .
C20 C 0.73943(19) -0.1143(2) 0.40007(15) 0.0324(5) Uani 1 1 d . . . . .
H20 H 0.759610 -0.206040 0.422957 0.039 Uiso 1 1 calc R . . . .
C21 C 0.82529(18) -0.0333(2) 0.37392(15) 0.0304(4) Uani 1 1 d . . . . .
C22 C 0.79328(19) 0.0985(2) 0.33654(15) 0.0316(5) Uani 1 1 d . . . . .
H22 H 0.850952 0.152682 0.316248 0.038 Uiso 1 1 calc R . . . .
C23 C 0.67830(19) 0.1510(2) 0.32876(15) 0.0314(5) Uani 1 1 d . . . . .
H23 H 0.656614 0.240721 0.302184 0.038 Uiso 1 1 calc R . . . .
O2 O 0.94320(13) -0.07390(17) 0.38148(11) 0.0379(4) Uani 1 1 d . . . . .
C24 C 0.9872(2) -0.1969(3) 0.4351(2) 0.0464(6) Uani 1 1 d . . . . .
H24A H 1.074016 -0.210585 0.439310 0.070 Uiso 1 1 calc GR . . . .
H24B H 0.938891 -0.275923 0.401446 0.070 Uiso 1 1 calc GR . . . .
H24C H 0.979175 -0.188941 0.501323 0.070 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.392(14) . ?
C1 C10 1.578(15) . ?
C1 N1 1.308(13) . ?
C6 C5 1.245(15) . ?
C6 C7 1.477(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(6) . ?
C3 C4 1.392(6) . ?
C3 C9 1.470(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.406(7) . ?
C5 H5 0.99(4) . ?
C7 H7 1.01(4) . ?
C7 C8 1.390(6) . ?
C8 H8 1.07(4) . ?
C8 C9 1.400(6) . ?
C9 C10 1.394(8) . ?
C10 H10 0.9500 . ?
N1 C11 1.421(3) . ?
N1 C18 1.433(3) . ?
C11 C12 1.386(3) . ?
C11 C16 1.392(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 C15 1.389(3) . ?
C14 O1 1.372(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9500 . ?
O1 C17 1.420(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.383(3) . ?
C18 C23 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.395(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C21 C22 1.389(3) . ?
C21 O2 1.371(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(3) . ?
C23 H23 0.9500 . ?
O2 C24 1.423(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 103.0(8) . . ?
N1 C1 C2 130.2(11) . . ?
N1 C1 C10 126.1(10) . . ?
C5 C6 C7 131.7(8) . . ?
C1 C2 H2 123.2 . . ?
C1 C2 C3 113.7(7) . . ?
C3 C2 H2 123.2 . . ?
C2 C3 C9 107.1(4) . . ?
C4 C3 C2 126.8(4) . . ?
C4 C3 C9 126.1(4) . . ?
C3 C4 H4 114.7 . . ?
C3 C4 C5 130.6(5) . . ?
C5 C4 H4 114.7 . . ?
C6 C5 C4 128.6(8) . . ?
C6 C5 H5 120(3) . . ?
C4 C5 H5 111(2) . . ?
C6 C7 H7 119(2) . . ?
C8 C7 C6 125.0(5) . . ?
C8 C7 H7 116(2) . . ?
C7 C8 H8 115(2) . . ?
C7 C8 C9 130.0(4) . . ?
C9 C8 H8 115(2) . . ?
C8 C9 C3 126.7(4) . . ?
C10 C9 C3 108.6(4) . . ?
C10 C9 C8 124.3(5) . . ?
C1 C10 H10 126.3 . . ?
C9 C10 C1 107.3(7) . . ?
C9 C10 H10 126.3 . . ?
C1 N1 C11 122.1(7) . . ?
C1 N1 C18 118.0(7) . . ?
C11 N1 C18 119.34(17) . . ?
C12 C11 N1 120.27(19) . . ?
C12 C11 C16 118.93(19) . . ?
C16 C11 N1 120.80(19) . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 119.71(19) . . ?
O1 C14 C13 124.54(19) . . ?
O1 C14 C15 115.74(19) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 120.05(19) . . ?
C15 C16 H16 120.0 . . ?
C14 O1 C17 117.38(17) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 N1 121.5(2) . . ?
C19 C18 C23 119.23(19) . . ?
C23 C18 N1 119.2(2) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 119.83(19) . . ?
O2 C21 C20 124.6(2) . . ?
O2 C21 C22 115.61(19) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C21 O2 C24 117.52(18) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
####################################################################### 
# 
# 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_2b-Br2
_database_code_depnum_ccdc_archive 'CCDC 2254134'
loop_
_audit_author_name
_audit_author_address
'Takahiro Tsuchiya'
;Kitasato University
Japan
;
_audit_update_record             
;
2023-07-12 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H32 Br2 N2 O4'
_chemical_formula_weight         740.47

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4361(3)
_cell_length_b                   17.0463(10)
_cell_length_c                   20.2087(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3250.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2466
_cell_measurement_theta_min      5.1690
_cell_measurement_theta_max      69.3870

_exptl_crystal_description       block
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.007
_exptl_absorpt_coefficient_mu    3.519
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8672
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.392
_diffrn_reflns_theta_max         67.493
_diffrn_reflns_theta_full        67.493
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.861
_reflns_number_total             5059
_reflns_number_gt                4208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.546
_reflns_Friedel_fraction_max     0.698
_reflns_Friedel_fraction_full    0.698

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²] 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 1288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5059
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Br45 Br 0.59417(8) 0.43816(5) 0.49068(4) 0.0351(2) Uani 1 1 d . . . . .
Br46 Br 0.51255(7) 0.57784(5) 0.74916(4) 0.0358(2) Uani 1 1 d . . . . .
O41 O 0.6288(6) 1.1417(3) 0.6197(3) 0.0387(13) Uani 1 1 d . . . . .
O24 O 0.0854(6) 0.2258(3) 0.5751(3) 0.0379(13) Uani 1 1 d . . . . .
O43 O 0.5171(6) 0.9550(3) 0.2302(3) 0.0411(13) Uani 1 1 d . . . . .
O26 O 0.9845(6) 0.3250(4) 0.8124(3) 0.0468(14) Uani 1 1 d . . . . .
N11 N 0.5364(6) 0.4220(4) 0.6517(3) 0.0330(14) Uani 1 1 d . . . . .
N28 N 0.5652(6) 0.8542(4) 0.4910(3) 0.0332(14) Uani 1 1 d . . . . .
C9 C 0.5666(7) 0.5969(5) 0.5473(4) 0.0297(16) Uani 1 1 d . . . . .
C32 C 0.5233(7) 0.9227(5) 0.2922(4) 0.0318(16) Uani 1 1 d . . . . .
C3 C 0.5492(7) 0.6310(5) 0.6124(4) 0.0276(16) Uani 1 1 d . . . . .
C29 C 0.5524(8) 0.8699(5) 0.4210(4) 0.0316(18) Uani 1 1 d . . . . .
C22 C 0.1942(8) 0.3570(5) 0.5792(4) 0.0330(18) Uani 1 1 d . . . . .
H22 H 0.118974 0.379441 0.556228 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3064(8) 0.4036(5) 0.5988(4) 0.0351(18) Uani 1 1 d . . . . .
H23 H 0.305159 0.456715 0.588449 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5637(7) 0.7799(5) 0.5181(4) 0.0326(17) Uani 1 1 d . . . . .
C34 C 0.6686(8) 0.9016(5) 0.3880(4) 0.0350(19) Uani 1 1 d . . . . .
H34 H 0.756310 0.904669 0.408843 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5778(7) 0.6359(4) 0.4869(4) 0.0319(16) Uani 1 1 d . . . . .
H8 H 0.587376 0.603826 0.449937 0.038 Uiso 1 1 calc R U . . .
C33 C 0.6522(8) 0.9282(5) 0.3244(4) 0.0358(18) Uani 1 1 d . . . . .
H33 H 0.729180 0.950346 0.302486 0.043 Uiso 1 1 calc R U . . .
C31 C 0.4082(9) 0.8878(5) 0.3242(4) 0.0355(17) Uani 1 1 d . . . . .
H31 H 0.321922 0.881893 0.302502 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5389(7) 0.5683(5) 0.6571(4) 0.0340(17) Uani 1 1 d . . . . .
C1 C 0.5479(7) 0.4975(5) 0.6237(4) 0.0293(17) Uani 1 1 d . . . . .
C4 C 0.5421(7) 0.7103(5) 0.6282(4) 0.0323(18) Uani 1 1 d . . . . .
H4 H 0.531817 0.721040 0.673045 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5662(8) 0.5149(4) 0.5568(4) 0.0286(16) Uani 1 1 d . . . . .
C30 C 0.4246(8) 0.8619(5) 0.3893(4) 0.0372(18) Uani 1 1 d . . . . .
H30 H 0.348474 0.839063 0.411272 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6513(8) 0.3945(5) 0.6917(4) 0.0304(17) Uani 1 1 d . . . . .
C38 C 0.6200(8) 1.0674(5) 0.5934(4) 0.0339(17) Uani 1 1 d . . . . .
C18 C 0.4202(8) 0.3735(4) 0.6332(4) 0.0314(16) Uani 1 1 d . . . . .
C5 C 0.5477(8) 0.7752(5) 0.5883(4) 0.0352(19) Uani 1 1 d . . . . .
H5 H 0.540114 0.823136 0.610047 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5767(8) 0.7163(5) 0.4742(4) 0.0337(17) Uani 1 1 d . . . . .
H7 H 0.586044 0.729946 0.429832 0.040 Uiso 1 1 calc R U . . .
C21 C 0.1918(8) 0.2774(5) 0.5931(4) 0.0314(17) Uani 1 1 d . . . . .
C35 C 0.5814(8) 0.9241(4) 0.5300(4) 0.0350(16) Uani 1 1 d . . . . .
C40 C 0.4711(8) 0.9788(5) 0.5320(4) 0.0351(18) Uani 1 1 d . . . . .
H40 H 0.384322 0.967273 0.512461 0.042 Uiso 1 1 calc R U . . .
C42 C 0.7611(8) 1.1635(5) 0.6497(5) 0.043(2) Uani 1 1 d . . . . .
H42A H 0.836229 1.157409 0.618089 0.064 Uiso 1 1 calc R U . . .
H42B H 0.778895 1.130464 0.687259 0.064 Uiso 1 1 calc R U . . .
H42C H 0.756547 1.217235 0.663770 0.064 Uiso 1 1 calc R U . . .
C15 C 0.8788(8) 0.3474(5) 0.7698(4) 0.039(2) Uani 1 1 d . . . . .
C17 C 0.7881(8) 0.4000(5) 0.6682(4) 0.0337(18) Uani 1 1 d . . . . .
H17 H 0.804124 0.419610 0.625894 0.040 Uiso 1 1 calc R U . . .
C20 C 0.3042(8) 0.2460(5) 0.6279(4) 0.0366(19) Uani 1 1 d . . . . .
H20 H 0.303448 0.192972 0.638576 0.044 Uiso 1 1 calc R U . . .
C36 C 0.7090(8) 0.9417(5) 0.5610(4) 0.0370(18) Uani 1 1 d . . . . .
H36 H 0.782171 0.905173 0.560511 0.044 Uiso 1 1 calc R U . . .
C25 C -0.0153(9) 0.2557(5) 0.5287(4) 0.042(2) Uani 1 1 d . . . . .
H25A H 0.033775 0.279543 0.492278 0.062 Uiso 1 1 calc R U . . .
H25B H -0.074083 0.294044 0.549999 0.062 Uiso 1 1 calc R U . . .
H25C H -0.073155 0.213435 0.512659 0.062 Uiso 1 1 calc R U . . .
C16 C 0.9025(9) 0.3768(5) 0.7069(4) 0.0366(18) Uani 1 1 d . . . . .
H16 H 0.994354 0.380936 0.690561 0.044 Uiso 1 1 calc R U . . .
C39 C 0.4912(9) 1.0497(5) 0.5631(4) 0.0383(18) Uani 1 1 d . . . . .
H39 H 0.418073 1.086297 0.563909 0.046 Uiso 1 1 calc R U . . .
C19 C 0.4192(8) 0.2923(5) 0.6474(4) 0.0338(17) Uani 1 1 d . . . . .
H19 H 0.494989 0.269642 0.669776 0.041 Uiso 1 1 calc R U . . .
C37 C 0.7284(8) 1.0129(5) 0.5928(4) 0.0351(19) Uani 1 1 d . . . . .
H37 H 0.813999 1.023952 0.613544 0.042 Uiso 1 1 calc R U . . .
C44 C 0.3855(9) 0.9523(6) 0.1959(4) 0.045(2) Uani 1 1 d . . . . .
H44A H 0.394528 0.979207 0.154379 0.068 Uiso 1 1 calc R U . . .
H44B H 0.313584 0.977257 0.222103 0.068 Uiso 1 1 calc R U . . .
H44C H 0.359544 0.898646 0.188041 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6281(8) 0.3655(5) 0.7553(4) 0.0399(18) Uani 1 1 d . . . . .
H13 H 0.536429 0.361558 0.771794 0.048 Uiso 1 1 calc R U . . .
C14 C 0.7421(9) 0.3425(6) 0.7937(4) 0.046(2) Uani 1 1 d . . . . .
H14 H 0.726385 0.323469 0.836155 0.055 Uiso 1 1 calc R U . . .
C27 C 1.1249(9) 0.3285(7) 0.7884(5) 0.059(3) Uani 1 1 d . . . . .
H27A H 1.132037 0.298705 0.748261 0.089 Uiso 1 1 calc R U . . .
H27B H 1.188181 0.307014 0.820934 0.089 Uiso 1 1 calc R U . . .
H27C H 1.149925 0.382106 0.779866 0.089 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br45 C10 1.888(7) . ?
Br46 C2 1.884(8) . ?
O41 C38 1.376(10) . ?
O41 C42 1.436(10) . ?
O24 C21 1.383(9) . ?
O24 C25 1.428(10) . ?
O43 C32 1.369(9) . ?
O43 C44 1.423(9) . ?
O26 C15 1.372(9) . ?
O26 C27 1.412(11) . ?
N11 C1 1.411(10) . ?
N11 C18 1.423(9) . ?
N11 C12 1.431(9) . ?
N28 C6 1.379(9) . ?
N28 C35 1.436(10) . ?
N28 C29 1.447(10) . ?
C9 C8 1.393(11) . ?
C9 C10 1.411(10) . ?
C9 C3 1.449(10) . ?
C32 C33 1.383(10) . ?
C32 C31 1.398(11) . ?
C3 C4 1.390(11) . ?
C3 C2 1.403(11) . ?
C29 C30 1.373(11) . ?
C29 C34 1.392(11) . ?
C22 C23 1.381(11) . ?
C22 C21 1.385(11) . ?
C23 C18 1.378(11) . ?
C6 C7 1.407(11) . ?
C6 C5 1.429(11) . ?
C34 C33 1.373(11) . ?
C8 C7 1.394(10) . ?
C31 C30 1.395(11) . ?
C2 C1 1.386(11) . ?
C1 C10 1.395(10) . ?
C4 C5 1.370(12) . ?
C12 C17 1.379(11) . ?
C12 C13 1.394(11) . ?
C38 C37 1.381(11) . ?
C38 C39 1.394(11) . ?
C18 C19 1.414(11) . ?
C21 C20 1.381(11) . ?
C35 C36 1.391(11) . ?
C35 C40 1.398(11) . ?
C40 C39 1.375(11) . ?
C15 C14 1.380(12) . ?
C15 C16 1.385(11) . ?
C17 C16 1.390(11) . ?
C20 C19 1.398(11) . ?
C36 C37 1.385(11) . ?
C13 C14 1.382(11) . ?

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
C38 O41 C42 117.0(6) . . ?
C21 O24 C25 115.4(6) . . ?
C32 O43 C44 118.1(6) . . ?
C15 O26 C27 117.1(7) . . ?
C1 N11 C18 118.9(6) . . ?
C1 N11 C12 117.8(6) . . ?
C18 N11 C12 122.8(6) . . ?
C6 N28 C35 123.1(6) . . ?
C6 N28 C29 123.9(6) . . ?
C35 N28 C29 113.0(6) . . ?
C8 C9 C10 126.3(7) . . ?
C8 C9 C3 127.8(7) . . ?
C10 C9 C3 105.9(7) . . ?
O43 C32 C33 116.1(7) . . ?
O43 C32 C31 124.2(7) . . ?
C33 C32 C31 119.7(7) . . ?
C4 C3 C2 126.2(7) . . ?
C4 C3 C9 127.1(7) . . ?
C2 C3 C9 106.7(7) . . ?
C30 C29 C34 120.5(7) . . ?
C30 C29 N28 120.8(7) . . ?
C34 C29 N28 118.3(7) . . ?
C23 C22 C21 121.1(7) . . ?
C18 C23 C22 121.9(8) . . ?
N28 C6 C7 117.2(7) . . ?
N28 C6 C5 116.5(7) . . ?
C7 C6 C5 126.3(7) . . ?
C33 C34 C29 119.2(7) . . ?
C9 C8 C7 129.0(7) . . ?
C34 C33 C32 121.1(7) . . ?
C30 C31 C32 119.0(7) . . ?
C1 C2 C3 110.3(7) . . ?
C1 C2 Br46 124.4(6) . . ?
C3 C2 Br46 125.4(6) . . ?
C2 C1 C10 107.2(7) . . ?
C2 C1 N11 126.5(7) . . ?
C10 C1 N11 126.3(7) . . ?
C5 C4 C3 130.5(8) . . ?
C1 C10 C9 110.0(7) . . ?
C1 C10 Br45 123.8(6) . . ?
C9 C10 Br45 126.1(6) . . ?
C29 C30 C31 120.4(8) . . ?
C17 C12 C13 119.2(7) . . ?
C17 C12 N11 119.5(7) . . ?
C13 C12 N11 121.2(6) . . ?
O41 C38 C37 125.3(7) . . ?
O41 C38 C39 114.9(7) . . ?
C37 C38 C39 119.8(8) . . ?
C23 C18 C19 117.5(7) . . ?
C23 C18 N11 121.1(7) . . ?
C19 C18 N11 121.3(7) . . ?
C4 C5 C6 129.3(8) . . ?
C8 C7 C6 129.9(7) . . ?
C20 C21 O24 116.4(7) . . ?
C20 C21 C22 118.1(7) . . ?
O24 C21 C22 125.5(7) . . ?
C36 C35 C40 119.1(7) . . ?
C36 C35 N28 121.2(7) . . ?
C40 C35 N28 119.4(7) . . ?
C39 C40 C35 119.8(7) . . ?
O26 C15 C14 116.3(7) . . ?
O26 C15 C16 124.1(7) . . ?
C14 C15 C16 119.6(8) . . ?
C12 C17 C16 120.9(8) . . ?
C21 C20 C19 121.4(8) . . ?
C37 C36 C35 120.9(8) . . ?
C15 C16 C17 119.6(8) . . ?
C40 C39 C38 120.7(8) . . ?
C20 C19 C18 120.0(7) . . ?
C38 C37 C36 119.7(7) . . ?
C14 C13 C12 119.7(7) . . ?
C15 C14 C13 120.9(8) . . ?

_refine_diff_density_max         0.751
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.083



####################################################################### 
# 
# 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_13br2_26(ph2n)2az
_database_code_depnum_ccdc_archive 'CCDC 2254133'
loop_
_audit_author_name
_audit_author_address
'Takahiro Tsuchiya'
;Kitasato University
Japan
;
_audit_update_record             
;
2023-07-12 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H24 Br2 N2'
_chemical_formula_weight         620.37

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'
Br Br -0.6763 1.2805 '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           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                   17.1091(3)
_cell_length_b                   9.5266(2)
_cell_length_c                   17.0439(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.493(2)
_cell_angle_gamma                90
_cell_volume                     2760.19(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8062
_cell_measurement_theta_min      5.1990
_cell_measurement_theta_max      74.5660

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.017
_exptl_absorpt_coefficient_mu    3.915
_shelx_estimated_absorpt_T_min   0.481
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63165
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  Rigaku_Synergy-S
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            15053
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.599
_diffrn_reflns_theta_max         67.998
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5018
_reflns_number_gt                4434
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+1.7695P] 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         5018
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
Br37 Br 0.81293(2) 0.65656(3) 0.79706(2) 0.02885(9) Uani 1 1 d . . . . .
Br38 Br 0.66019(2) 0.60004(3) 0.47704(2) 0.02732(9) Uani 1 1 d . . . . .
N11 N 0.39983(12) 0.6461(2) 0.77204(12) 0.0223(4) Uani 1 1 d . . . . .
N24 N 0.82176(12) 0.6153(2) 0.60353(13) 0.0258(4) Uani 1 1 d . . . . .
C12 C 0.39290(14) 0.6221(2) 0.85431(14) 0.0219(5) Uani 1 1 d . . . . .
C4 C 0.65355(14) 0.6418(2) 0.71745(14) 0.0206(5) Uani 1 1 d . . . . .
C1 C 0.47147(14) 0.6465(2) 0.74257(14) 0.0205(5) Uani 1 1 d . . . . .
C2 C 0.53928(15) 0.6627(2) 0.79821(14) 0.0236(5) Uani 1 1 d . . . . .
H2 H 0.529015 0.677906 0.851178 0.028 Uiso 1 1 calc R U . . .
C3 C 0.61745(15) 0.6598(2) 0.78675(14) 0.0225(5) Uani 1 1 d . . . . .
H3 H 0.652883 0.671946 0.833332 0.027 Uiso 1 1 calc R U . . .
C10 C 0.47096(14) 0.6318(2) 0.65977(14) 0.0224(5) Uani 1 1 d . . . . .
H10 H 0.420213 0.625519 0.630945 0.027 Uiso 1 1 calc R U . . .
C18 C 0.32634(14) 0.6537(2) 0.72159(13) 0.0211(5) Uani 1 1 d . . . . .
C8 C 0.61374(14) 0.6290(2) 0.63648(14) 0.0204(5) Uani 1 1 d . . . . .
C13 C 0.36410(15) 0.7279(3) 0.89945(15) 0.0260(5) Uani 1 1 d . . . . .
H13 H 0.351125 0.817257 0.876835 0.031 Uiso 1 1 calc R U . . .
C6 C 0.74799(15) 0.6243(2) 0.63228(14) 0.0230(5) Uani 1 1 d . . . . .
C9 C 0.53324(14) 0.6254(2) 0.61438(13) 0.0213(5) Uani 1 1 d . . . . .
H9 H 0.518315 0.617029 0.559173 0.026 Uiso 1 1 calc R U . . .
C7 C 0.67384(15) 0.6196(2) 0.58751(14) 0.0222(5) Uani 1 1 d . . . . .
C25 C 0.84786(15) 0.7308(3) 0.56080(14) 0.0251(5) Uani 1 1 d . . . . .
C17 C 0.41287(16) 0.4919(3) 0.88762(15) 0.0276(5) Uani 1 1 d . . . . .
H17 H 0.432553 0.419806 0.856740 0.033 Uiso 1 1 calc R U . . .
C31 C 0.87359(15) 0.5068(3) 0.63398(14) 0.0261(5) Uani 1 1 d . . . . .
C5 C 0.73408(15) 0.6388(2) 0.71141(14) 0.0239(5) Uani 1 1 d . . . . .
C19 C 0.28189(15) 0.5336(3) 0.70521(15) 0.0275(5) Uani 1 1 d . . . . .
H19 H 0.299083 0.446300 0.727874 0.033 Uiso 1 1 calc R U . . .
C30 C 0.90286(16) 0.7111(3) 0.50714(15) 0.0301(5) Uani 1 1 d . . . . .
H30 H 0.921533 0.619528 0.497412 0.036 Uiso 1 1 calc R U . . .
C23 C 0.30044(16) 0.7824(3) 0.69079(15) 0.0281(5) Uani 1 1 d . . . . .
H23 H 0.330548 0.864810 0.703244 0.034 Uiso 1 1 calc R U . . .
C26 C 0.81822(16) 0.8649(3) 0.57152(16) 0.0303(5) Uani 1 1 d . . . . .
H26 H 0.779803 0.878990 0.606862 0.036 Uiso 1 1 calc R U . . .
C16 C 0.40379(17) 0.4685(3) 0.96619(16) 0.0325(6) Uani 1 1 d . . . . .
H16 H 0.418057 0.380190 0.989499 0.039 Uiso 1 1 calc R U . . .
C36 C 0.95370(16) 0.5302(3) 0.65360(16) 0.0318(6) Uani 1 1 d . . . . .
H36 H 0.975792 0.619431 0.644469 0.038 Uiso 1 1 calc R U . . .
C32 C 0.84259(17) 0.3752(3) 0.64767(17) 0.0328(6) Uani 1 1 d . . . . .
H32 H 0.788098 0.357697 0.633898 0.039 Uiso 1 1 calc R U . . .
C14 C 0.35452(17) 0.7015(3) 0.97797(16) 0.0321(6) Uani 1 1 d . . . . .
H14 H 0.334370 0.772767 1.009111 0.038 Uiso 1 1 calc R U . . .
C29 C 0.93011(16) 0.8260(3) 0.46807(16) 0.0352(6) Uani 1 1 d . . . . .
H29 H 0.969075 0.812915 0.433207 0.042 Uiso 1 1 calc R U . . .
C22 C 0.23019(18) 0.7897(3) 0.64164(16) 0.0347(6) Uani 1 1 d . . . . .
H22 H 0.212202 0.877488 0.620236 0.042 Uiso 1 1 calc R U . . .
C21 C 0.18632(16) 0.6703(3) 0.62366(16) 0.0344(6) Uani 1 1 d . . . . .
H21 H 0.138506 0.675782 0.589538 0.041 Uiso 1 1 calc R U . . .
C15 C 0.37423(17) 0.5720(3) 1.01087(15) 0.0335(6) Uani 1 1 d . . . . .
H15 H 0.367366 0.554265 1.064511 0.040 Uiso 1 1 calc R U . . .
C20 C 0.21199(16) 0.5419(3) 0.65541(16) 0.0327(6) Uani 1 1 d . . . . .
H20 H 0.181703 0.459590 0.643053 0.039 Uiso 1 1 calc R U . . .
C27 C 0.84510(17) 0.9782(3) 0.53024(17) 0.0362(6) Uani 1 1 d . . . . .
H27 H 0.824523 1.069407 0.537342 0.043 Uiso 1 1 calc R U . . .
C35 C 1.00085(18) 0.4230(4) 0.68641(18) 0.0420(7) Uani 1 1 d . . . . .
H35 H 1.055591 0.439022 0.699389 0.050 Uiso 1 1 calc R U . . .
C28 C 0.90121(17) 0.9592(3) 0.47929(17) 0.0375(6) Uani 1 1 d . . . . .
H28 H 0.919943 1.037087 0.452034 0.045 Uiso 1 1 calc R U . . .
C33 C 0.8911(2) 0.2691(3) 0.68145(19) 0.0426(7) Uani 1 1 d . . . . .
H33 H 0.869484 0.179766 0.691184 0.051 Uiso 1 1 calc R U . . .
C34 C 0.9699(2) 0.2925(4) 0.70076(19) 0.0454(8) Uani 1 1 d . . . . .
H34 H 1.002977 0.219929 0.723783 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br37 C5 1.880(2) . ?
Br38 C7 1.880(2) . ?
N11 C1 1.376(3) . ?
N11 C12 1.439(3) . ?
N11 C18 1.443(3) . ?
N24 C6 1.407(3) . ?
N24 C25 1.419(3) . ?
N24 C31 1.421(3) . ?
C12 C17 1.391(4) . ?
C12 C13 1.392(3) . ?
C4 C5 1.393(3) . ?
C4 C3 1.404(3) . ?
C4 C8 1.473(3) . ?
C1 C10 1.417(3) . ?
C1 C2 1.421(4) . ?
C2 C3 1.374(4) . ?
C10 C9 1.387(3) . ?
C18 C19 1.384(4) . ?
C18 C23 1.386(3) . ?
C8 C9 1.387(3) . ?
C8 C7 1.399(3) . ?
C13 C14 1.389(4) . ?
C6 C5 1.403(3) . ?
C6 C7 1.405(4) . ?
C25 C26 1.394(4) . ?
C25 C30 1.397(4) . ?
C17 C16 1.384(4) . ?
C31 C36 1.391(4) . ?
C31 C32 1.392(4) . ?
C19 C20 1.388(4) . ?
C30 C29 1.389(4) . ?
C23 C22 1.387(4) . ?
C26 C27 1.395(4) . ?
C16 C15 1.377(4) . ?
C36 C35 1.381(4) . ?
C32 C33 1.391(4) . ?
C14 C15 1.382(4) . ?
C29 C28 1.383(5) . ?
C22 C21 1.378(4) . ?
C21 C20 1.389(4) . ?
C27 C28 1.377(4) . ?
C35 C34 1.383(5) . ?
C33 C34 1.369(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N11 C12 122.1(2) . . ?
C1 N11 C18 122.32(19) . . ?
C12 N11 C18 115.25(19) . . ?
C6 N24 C25 118.6(2) . . ?
C6 N24 C31 117.6(2) . . ?
C25 N24 C31 122.1(2) . . ?
C17 C12 C13 120.4(2) . . ?
C17 C12 N11 119.7(2) . . ?
C13 C12 N11 119.8(2) . . ?
C5 C4 C3 126.7(2) . . ?
C5 C4 C8 106.6(2) . . ?
C3 C4 C8 126.7(2) . . ?
N11 C1 C10 117.2(2) . . ?
N11 C1 C2 116.8(2) . . ?
C10 C1 C2 126.0(2) . . ?
C3 C2 C1 129.6(2) . . ?
C2 C3 C4 130.6(2) . . ?
C9 C10 C1 129.9(2) . . ?
C19 C18 C23 120.6(2) . . ?
C19 C18 N11 120.1(2) . . ?
C23 C18 N11 119.3(2) . . ?
C9 C8 C7 127.7(2) . . ?
C9 C8 C4 126.6(2) . . ?
C7 C8 C4 105.7(2) . . ?
C14 C13 C12 119.3(2) . . ?
C5 C6 C7 106.5(2) . . ?
C5 C6 N24 126.7(2) . . ?
C7 C6 N24 126.8(2) . . ?
C8 C9 C10 130.5(2) . . ?
C8 C7 C6 110.7(2) . . ?
C8 C7 Br38 125.98(19) . . ?
C6 C7 Br38 123.32(18) . . ?
C26 C25 C30 119.4(2) . . ?
C26 C25 N24 120.2(2) . . ?
C30 C25 N24 120.4(2) . . ?
C16 C17 C12 119.3(2) . . ?
C36 C31 C32 119.2(3) . . ?
C36 C31 N24 121.9(2) . . ?
C32 C31 N24 118.9(2) . . ?
C4 C5 C6 110.5(2) . . ?
C4 C5 Br37 124.72(19) . . ?
C6 C5 Br37 124.80(19) . . ?
C18 C19 C20 119.5(2) . . ?
C29 C30 C25 119.7(3) . . ?
C18 C23 C22 119.4(3) . . ?
C25 C26 C27 119.9(3) . . ?
C15 C16 C17 120.5(2) . . ?
C35 C36 C31 119.6(3) . . ?
C33 C32 C31 120.2(3) . . ?
C15 C14 C13 120.2(2) . . ?
C28 C29 C30 120.8(3) . . ?
C21 C22 C23 120.4(2) . . ?
C22 C21 C20 120.0(3) . . ?
C16 C15 C14 120.2(2) . . ?
C19 C20 C21 120.0(3) . . ?
C28 C27 C26 120.6(3) . . ?
C36 C35 C34 121.2(3) . . ?
C27 C28 C29 119.6(3) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C35 119.4(3) . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.073



