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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_az_k4
_database_code_depnum_ccdc_archive 'CCDC 1861441'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_audit_creation_date             2018-08-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
2,3-bis(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)phenyl)quinoxaline
_chemical_formula_moiety         '0.22(C3 H6 O), 0.22(C48 H36 N4)'
_chemical_formula_sum            'C11.33 H9.33 N0.89 O0.22'
_chemical_formula_weight         161.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.1633(11)
_cell_length_b                   12.2381(14)
_cell_length_c                   15.3155(16)
_cell_angle_alpha                102.079(9)
_cell_angle_beta                 93.931(9)
_cell_angle_gamma                93.152(9)
_cell_volume                     2036.1(4)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    2239
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.5830
_cell_measurement_theta_min      2.3990
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             768
_exptl_crystal_preparation       
'single crystal was grown from solvents mixture (DCM, acetone)'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, acetone'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.1097
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12143
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.943
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     85.00 111.00   1.00   35.00    --   30.10  54.00  60.00   26
  2  ω    -72.00  34.00   1.00   35.00    --   30.10  54.00-180.00  106
  3  ω    -73.00  32.00   1.00   35.00    --   30.10  54.00 -60.00  105
  4  ω    -72.00  33.00   1.00   35.00    --   30.10  54.00  60.00  105
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0140920000
_diffrn_orient_matrix_UB_12      -0.0300800000
_diffrn_orient_matrix_UB_13      -0.0447422000
_diffrn_orient_matrix_UB_21      0.0144476000
_diffrn_orient_matrix_UB_22      0.0492138000
_diffrn_orient_matrix_UB_23      -0.0158109000
_diffrn_orient_matrix_UB_31      0.0605760000
_diffrn_orient_matrix_UB_32      -0.0142843000
_diffrn_orient_matrix_UB_33      -0.0025305000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3625
_reflns_number_total             8014
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8014
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1725
_refine_ls_R_factor_gt           0.0771
_refine_ls_restrained_S_all      0.990
_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)+(0.1148P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1958
_refine_ls_wR_factor_ref         0.2679
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C41(H41A,H41B), C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20), C25(H25), C26(H26), C27(H27), C28(H28),
  C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C38(H38),
 C39(H39), C44(H44), C45(H45), C46(H46), C47(H47)
2.c Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C51(H51A,H51B,H51C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3663(9) 0.0807(6) -0.0841(5) 0.258(4) Uani 1 1 d . . . . .
C49 C 0.4743(9) -0.0519(8) -0.1454(6) 0.173(4) Uani 1 1 d . . . . .
H49A H 0.521955 -0.042606 -0.193484 0.259 Uiso 1 1 calc GR . . . .
H49B H 0.446867 -0.129291 -0.153132 0.259 Uiso 1 1 calc GR . . . .
H49C H 0.522112 -0.028225 -0.089330 0.259 Uiso 1 1 calc GR . . . .
C50 C 0.3784(13) 0.0108(6) -0.1455(7) 0.178(5) Uani 1 1 d . . . . .
C51 C 0.2660(11) -0.0159(8) -0.2136(8) 0.228(6) Uani 1 1 d . . . . .
H51A H 0.194907 -0.000386 -0.182574 0.343 Uiso 1 1 calc GR . . . .
H51B H 0.261591 -0.093506 -0.243084 0.343 Uiso 1 1 calc GR . . . .
H51C H 0.271817 0.029773 -0.257242 0.343 Uiso 1 1 calc GR . . . .
N1 N 0.3240(3) 0.6395(3) 0.1709(2) 0.0535(8) Uani 1 1 d . . . . .
N2 N 0.6814(3) 0.9229(3) 0.4850(2) 0.0559(8) Uani 1 1 d . . . . .
N3 N 0.6555(3) 0.8788(3) 0.6567(2) 0.0528(8) Uani 1 1 d . . . . .
N4 N 0.1904(2) 0.5821(3) 0.6957(2) 0.0488(8) Uani 1 1 d . . . . .
C1 C 0.2565(4) 0.7028(4) 0.1187(3) 0.0617(11) Uani 1 1 d . . . . .
C2 C 0.3132(5) 0.7648(5) 0.0658(3) 0.0881(15) Uani 1 1 d . . . . .
H2 H 0.396347 0.767268 0.063861 0.106 Uiso 1 1 calc R . . . .
C3 C 0.2419(7) 0.8244(5) 0.0148(4) 0.115(2) Uani 1 1 d . . . . .
H3 H 0.277281 0.866120 -0.022116 0.138 Uiso 1 1 calc R . . . .
C4 C 0.1197(7) 0.8198(6) 0.0204(5) 0.120(2) Uani 1 1 d . . . . .
H4 H 0.072531 0.860263 -0.012005 0.144 Uiso 1 1 calc R . . . .
C5 C 0.0669(5) 0.7581(5) 0.0716(4) 0.0985(18) Uani 1 1 d . . . . .
H5 H -0.016501 0.755012 0.072137 0.118 Uiso 1 1 calc R . . . .
C6 C 0.1319(4) 0.6992(4) 0.1237(3) 0.0669(12) Uani 1 1 d . . . . .
C7 C 0.0775(4) 0.6286(4) 0.1819(3) 0.0763(13) Uani 1 1 d . . . . .
H7A H -0.005401 0.646312 0.188947 0.092 Uiso 1 1 calc R . . . .
H7B H 0.120791 0.647141 0.240799 0.092 Uiso 1 1 calc R . . . .
C8 C 0.0806(4) 0.5043(4) 0.1442(3) 0.0768(14) Uani 1 1 d . . . . .
H8A H 0.040382 0.464775 0.183792 0.092 Uiso 1 1 calc R . . . .
H8B H 0.033259 0.486750 0.086851 0.092 Uiso 1 1 calc R . . . .
C9 C 0.2008(4) 0.4577(4) 0.1304(3) 0.0595(10) Uani 1 1 d . . . . .
C10 C 0.2023(5) 0.3407(4) 0.1011(3) 0.0741(13) Uani 1 1 d . . . . .
H10 H 0.130183 0.296840 0.094063 0.089 Uiso 1 1 calc R . . . .
C11 C 0.3053(6) 0.2902(5) 0.0829(3) 0.0938(17) Uani 1 1 d . . . . .
H11 H 0.302767 0.212846 0.062793 0.113 Uiso 1 1 calc R . . . .
C12 C 0.4133(5) 0.3523(5) 0.0938(3) 0.0872(16) Uani 1 1 d . . . . .
H12 H 0.484035 0.317287 0.081929 0.105 Uiso 1 1 calc R . . . .
C13 C 0.4165(4) 0.4663(4) 0.1223(3) 0.0695(12) Uani 1 1 d . . . . .
H13 H 0.489633 0.508439 0.128375 0.083 Uiso 1 1 calc R . . . .
C14 C 0.3115(3) 0.5203(3) 0.1423(2) 0.0531(9) Uani 1 1 d . . . . .
C15 C 0.3870(3) 0.6917(3) 0.2533(3) 0.0483(9) Uani 1 1 d . . . . .
C16 C 0.4115(3) 0.8076(3) 0.2760(3) 0.0560(10) Uani 1 1 d . . . . .
H16 H 0.383932 0.851786 0.237388 0.067 Uiso 1 1 calc R . . . .
C17 C 0.4764(3) 0.8568(3) 0.3558(3) 0.0549(10) Uani 1 1 d . . . . .
H17 H 0.494219 0.933906 0.368461 0.066 Uiso 1 1 calc R . . . .
C18 C 0.5164(3) 0.7961(3) 0.4180(2) 0.0432(8) Uani 1 1 d . . . . .
C19 C 0.4877(3) 0.6812(3) 0.3962(2) 0.0464(9) Uani 1 1 d . . . . .
H19 H 0.511269 0.638022 0.436745 0.056 Uiso 1 1 calc R . . . .
C20 C 0.4252(3) 0.6293(3) 0.3160(2) 0.0512(9) Uani 1 1 d . . . . .
H20 H 0.408197 0.552124 0.303332 0.061 Uiso 1 1 calc R . . . .
C21 C 0.5933(3) 0.8532(3) 0.4986(2) 0.0448(8) Uani 1 1 d . . . . .
C22 C 0.5777(3) 0.8343(3) 0.5876(2) 0.0446(8) Uani 1 1 d . . . . .
C23 C 0.7604(3) 0.9716(3) 0.5560(3) 0.0569(10) Uani 1 1 d . . . . .
C24 C 0.7492(3) 0.9483(3) 0.6420(3) 0.0553(10) Uani 1 1 d . . . . .
C25 C 0.8344(4) 0.9965(4) 0.7136(4) 0.0749(13) Uani 1 1 d . . . . .
H25 H 0.826238 0.982515 0.770370 0.090 Uiso 1 1 calc R . . . .
C26 C 0.9295(4) 1.0645(4) 0.6989(4) 0.0885(16) Uani 1 1 d . . . . .
H26 H 0.987016 1.095161 0.745737 0.106 Uiso 1 1 calc R . . . .
C27 C 0.9407(4) 1.0881(4) 0.6140(5) 0.0899(17) Uani 1 1 d . . . . .
H27 H 1.005468 1.134749 0.605520 0.108 Uiso 1 1 calc R . . . .
C28 C 0.8582(4) 1.0439(4) 0.5434(4) 0.0787(14) Uani 1 1 d . . . . .
H28 H 0.866302 1.061127 0.487634 0.094 Uiso 1 1 calc R . . . .
C29 C 0.4740(3) 0.7639(3) 0.6091(2) 0.0441(8) Uani 1 1 d . . . . .
C30 C 0.4947(3) 0.6971(3) 0.6710(3) 0.0505(9) Uani 1 1 d . . . . .
H30 H 0.572858 0.693795 0.695091 0.061 Uiso 1 1 calc R . . . .
C31 C 0.4021(3) 0.6355(3) 0.6975(3) 0.0508(9) Uani 1 1 d . . . . .
H31 H 0.419092 0.588596 0.736616 0.061 Uiso 1 1 calc R . . . .
C32 C 0.2826(3) 0.6430(3) 0.6662(2) 0.0440(8) Uani 1 1 d . . . . .
C33 C 0.2618(3) 0.7118(3) 0.6048(2) 0.0453(8) Uani 1 1 d . . . . .
H33 H 0.183468 0.718288 0.582619 0.054 Uiso 1 1 calc R . . . .
C34 C 0.3560(3) 0.7700(3) 0.5768(2) 0.0474(9) Uani 1 1 d . . . . .
H34 H 0.339980 0.814165 0.535473 0.057 Uiso 1 1 calc R . . . .
C35 C 0.2174(3) 0.4974(3) 0.7450(3) 0.0485(9) Uani 1 1 d . . . . .
C36 C 0.2399(3) 0.5232(4) 0.8378(3) 0.0599(10) Uani 1 1 d . . . . .
H36 H 0.237366 0.596516 0.869594 0.072 Uiso 1 1 calc R . . . .
C37 C 0.2660(4) 0.4390(5) 0.8821(3) 0.0679(12) Uani 1 1 d . . . . .
H37 H 0.280053 0.455891 0.944165 0.082 Uiso 1 1 calc R . . . .
C38 C 0.2713(4) 0.3314(5) 0.8360(3) 0.0737(13) Uani 1 1 d . . . . .
H38 H 0.290691 0.275624 0.866435 0.088 Uiso 1 1 calc R . . . .
C39 C 0.2478(4) 0.3055(4) 0.7435(3) 0.0671(12) Uani 1 1 d . . . . .
H39 H 0.251045 0.231942 0.712300 0.080 Uiso 1 1 calc R . . . .
C40 C 0.2196(3) 0.3875(3) 0.6969(3) 0.0531(10) Uani 1 1 d . . . . .
C41 C 0.1829(3) 0.3634(4) 0.5981(3) 0.0595(10) Uani 1 1 d . . . . .
H41A H 0.200189 0.287382 0.571463 0.071 Uiso 1 1 calc R . . . .
H41B H 0.229375 0.413983 0.570230 0.071 Uiso 1 1 calc R . . . .
C42 C 0.0484(3) 0.3775(3) 0.5806(3) 0.0580(10) Uani 1 1 d . . . . .
H42A H 0.029538 0.359952 0.516244 0.070 Uiso 1 1 calc R . . . .
H42B H 0.004358 0.321215 0.604383 0.070 Uiso 1 1 calc R . . . .
C43 C -0.0010(3) 0.4888(3) 0.6170(2) 0.0446(8) Uani 1 1 d . . . . .
C44 C -0.1245(3) 0.4956(4) 0.6016(3) 0.0574(10) Uani 1 1 d . . . . .
H44 H -0.171257 0.431963 0.571358 0.069 Uiso 1 1 calc R . . . .
C45 C -0.1797(4) 0.5934(4) 0.6297(3) 0.0652(12) Uani 1 1 d . . . . .
H45 H -0.262178 0.595572 0.617443 0.078 Uiso 1 1 calc R . . . .
C46 C -0.1130(4) 0.6869(4) 0.6756(3) 0.0653(12) Uani 1 1 d . . . . .
H46 H -0.149612 0.753369 0.693922 0.078 Uiso 1 1 calc R . . . .
C47 C 0.0093(3) 0.6829(3) 0.6947(3) 0.0568(10) Uani 1 1 d . . . . .
H47 H 0.054424 0.746533 0.726792 0.068 Uiso 1 1 calc R . . . .
C48 C 0.0656(3) 0.5839(3) 0.6663(2) 0.0459(9) 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
O1 C50 1.152(8) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C49 C50 1.351(12) . ?
C50 C51 1.549(14) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
N1 C1 1.431(5) . ?
N1 C14 1.429(5) . ?
N1 C15 1.409(5) . ?
N2 C21 1.323(4) . ?
N2 C23 1.362(5) . ?
N3 C22 1.324(4) . ?
N3 C24 1.372(5) . ?
N4 C32 1.394(4) . ?
N4 C35 1.438(4) . ?
N4 C48 1.438(4) . ?
C1 C2 1.381(6) . ?
C1 C6 1.397(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.411(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.340(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(6) . ?
C6 C7 1.500(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.513(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.497(6) . ?
C9 C10 1.410(6) . ?
C9 C14 1.398(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.354(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.398(5) . ?
C15 C16 1.394(5) . ?
C15 C20 1.406(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(5) . ?
C18 C19 1.390(5) . ?
C18 C21 1.475(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.450(5) . ?
C22 C29 1.501(5) . ?
C23 C24 1.417(6) . ?
C23 C28 1.416(5) . ?
C24 C25 1.407(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.372(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.402(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.370(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.392(5) . ?
C29 C34 1.386(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.379(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.400(5) . ?
C32 C33 1.404(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.379(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.391(5) . ?
C35 C40 1.393(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.381(6) . ?
C37 H37 0.9300 . ?
C37 C38 1.365(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.389(6) . ?
C39 H39 0.9300 . ?
C39 C40 1.386(5) . ?
C40 C41 1.503(5) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.533(5) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.509(5) . ?
C43 C44 1.392(5) . ?
C43 C48 1.392(5) . ?
C44 H44 0.9300 . ?
C44 C45 1.379(6) . ?
C45 H45 0.9300 . ?
C45 C46 1.362(6) . ?
C46 H46 0.9300 . ?
C46 C47 1.382(5) . ?
C47 H47 0.9300 . ?
C47 C48 1.398(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
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C50 C49 H49A 109.5 . . ?
C50 C49 H49B 109.5 . . ?
C50 C49 H49C 109.5 . . ?
O1 C50 C49 119.8(14) . . ?
O1 C50 C51 113.5(12) . . ?
C49 C50 C51 125.6(9) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C14 N1 C1 117.1(3) . . ?
C15 N1 C1 121.1(3) . . ?
C15 N1 C14 121.3(3) . . ?
C21 N2 C23 118.0(3) . . ?
C22 N3 C24 117.4(3) . . ?
C32 N4 C35 120.6(3) . . ?
C32 N4 C48 123.2(3) . . ?
C35 N4 C48 115.3(3) . . ?
C2 C1 N1 120.9(4) . . ?
C2 C1 C6 121.8(4) . . ?
C6 C1 N1 117.3(4) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(5) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(6) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.2(6) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C7 118.3(4) . . ?
C5 C6 C1 117.2(4) . . ?
C5 C6 C7 124.5(4) . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C6 C7 C8 112.8(4) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8A 107.8 . . ?
C7 C8 H8B 107.8 . . ?
H8A C8 H8B 107.1 . . ?
C9 C8 C7 118.1(4) . . ?
C9 C8 H8A 107.8 . . ?
C9 C8 H8B 107.8 . . ?
C10 C9 C8 117.2(4) . . ?
C14 C9 C8 125.7(4) . . ?
C14 C9 C10 117.1(4) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.2(5) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(5) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(5) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 N1 123.4(3) . . ?
C9 C14 C13 119.7(4) . . ?
C13 C14 N1 116.8(4) . . ?
C16 C15 N1 121.0(3) . . ?
C16 C15 C20 117.7(4) . . ?
C20 C15 N1 121.3(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 118.6 . . ?
C16 C17 C18 122.8(4) . . ?
C18 C17 H17 118.6 . . ?
C17 C18 C21 119.7(3) . . ?
C19 C18 C17 116.6(3) . . ?
C19 C18 C21 123.5(3) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.9(3) . . ?
C20 C19 H19 119.1 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
N2 C21 C18 115.7(3) . . ?
N2 C21 C22 120.7(3) . . ?
C22 C21 C18 123.6(3) . . ?
N3 C22 C21 121.7(3) . . ?
N3 C22 C29 114.8(3) . . ?
C21 C22 C29 123.5(3) . . ?
N2 C23 C24 121.2(3) . . ?
N2 C23 C28 119.6(4) . . ?
C28 C23 C24 119.1(4) . . ?
N3 C24 C23 120.7(4) . . ?
N3 C24 C25 119.1(4) . . ?
C25 C24 C23 120.2(4) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.4(5) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.6(5) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.4(5) . . ?
C28 C27 H27 119.3 . . ?
C23 C28 H28 120.3 . . ?
C27 C28 C23 119.3(5) . . ?
C27 C28 H28 120.3 . . ?
C30 C29 C22 118.8(3) . . ?
C34 C29 C22 123.2(3) . . ?
C34 C29 C30 117.7(3) . . ?
C29 C30 H30 119.2 . . ?
C31 C30 C29 121.6(3) . . ?
C31 C30 H30 119.2 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.7(3) . . ?
C32 C31 H31 119.7 . . ?
N4 C32 C31 119.5(3) . . ?
N4 C32 C33 122.9(3) . . ?
C31 C32 C33 117.6(3) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 C32 120.9(3) . . ?
C34 C33 H33 119.5 . . ?
C29 C34 H34 119.3 . . ?
C33 C34 C29 121.4(3) . . ?
C33 C34 H34 119.3 . . ?
C36 C35 N4 121.5(4) . . ?
C36 C35 C40 120.7(4) . . ?
C40 C35 N4 117.8(3) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 C35 119.4(4) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 119.6 . . ?
C38 C37 C36 120.9(4) . . ?
C38 C37 H37 119.6 . . ?
C37 C38 H38 120.1 . . ?
C37 C38 C39 119.7(4) . . ?
C39 C38 H38 120.1 . . ?
C38 C39 H39 119.5 . . ?
C40 C39 C38 121.0(5) . . ?
C40 C39 H39 119.5 . . ?
C35 C40 C41 118.0(3) . . ?
C39 C40 C35 118.4(4) . . ?
C39 C40 C41 123.5(4) . . ?
C40 C41 H41A 109.4 . . ?
C40 C41 H41B 109.4 . . ?
C40 C41 C42 111.0(3) . . ?
H41A C41 H41B 108.0 . . ?
C42 C41 H41A 109.4 . . ?
C42 C41 H41B 109.4 . . ?
C41 C42 H42A 107.5 . . ?
C41 C42 H42B 107.5 . . ?
H42A C42 H42B 107.0 . . ?
C43 C42 C41 119.4(3) . . ?
C43 C42 H42A 107.5 . . ?
C43 C42 H42B 107.5 . . ?
C44 C43 C42 116.9(3) . . ?
C44 C43 C48 117.5(3) . . ?
C48 C43 C42 125.6(3) . . ?
C43 C44 H44 118.9 . . ?
C45 C44 C43 122.2(4) . . ?
C45 C44 H44 118.9 . . ?
C44 C45 H45 120.1 . . ?
C46 C45 C44 119.7(4) . . ?
C46 C45 H45 120.1 . . ?
C45 C46 H46 120.0 . . ?
C45 C46 C47 119.9(4) . . ?
C47 C46 H46 120.0 . . ?
C46 C47 H47 119.7 . . ?
C46 C47 C48 120.5(4) . . ?
C48 C47 H47 119.7 . . ?
C43 C48 N4 122.0(3) . . ?
C43 C48 C47 120.1(3) . . ?
C47 C48 N4 117.7(3) . . ?

_olex2_exptl_crystal_mounting_method 'using glass capillary and glue'
_olex2_submission_original_sample_id AZ_
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.131
_oxdiff_exptl_absorpt_empirical_full_min 0.716
####################################################################### 
# 
# 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_isb_2
_database_code_depnum_ccdc_archive 'CCDC 1861442'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_audit_creation_date             2018-08-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
2,3-bis(4-(5H-dibenzo[b,f]azepin-5-yl)phenyl)quinoxaline
_chemical_formula_moiety         '0.2(C48 H32 N4)'
_chemical_formula_sum            'C9.60 H6.40 N0.80'
_chemical_formula_weight         132.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.135(4)
_cell_length_b                   12.225(3)
_cell_length_c                   17.067(4)
_cell_angle_alpha                78.98(2)
_cell_angle_beta                 81.21(2)
_cell_angle_gamma                67.65(3)
_cell_volume                     2289.4(12)
_cell_formula_units_Z            10
_cell_measurement_reflns_used    1540
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6880
_cell_measurement_theta_min      2.1920
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.964
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_preparation       
'material was dissolved in DCM and acetone mixture. Then the same amount of hexane was added.'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, acetone, hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_unetI/netI     0.1762
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.039
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  33.00   1.00   90.00    --   30.10  54.00 -30.00  104
  2  ω    -72.00 -47.00   1.00   90.00    --   30.10  54.00  90.00   25
  3  ω     20.00  46.00   1.00   90.00    --   30.10  54.00  90.00   26
  4  ω    -74.00 108.00   1.00   90.00    --   30.10  54.00-150.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0004450000
_diffrn_orient_matrix_UB_12      -0.0570897000
_diffrn_orient_matrix_UB_13      0.0182077000
_diffrn_orient_matrix_UB_21      0.0626376000
_diffrn_orient_matrix_UB_22      -0.0207127000
_diffrn_orient_matrix_UB_23      0.0025076000
_diffrn_orient_matrix_UB_31      -0.0101030000
_diffrn_orient_matrix_UB_32      0.0182428000
_diffrn_orient_matrix_UB_33      0.0383270000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2705
_reflns_number_total             8986
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8986
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1816
_refine_ls_R_factor_gt           0.0764
_refine_ls_restrained_S_all      0.868
_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)+(0.0780P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1913
_refine_ls_wR_factor_ref         0.2580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
  C26(H26), C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37),
 C38(H38), C39(H39), C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6127(3) 1.0275(3) 0.59497(19) 0.0565(9) Uani 1 1 d . . . . .
N2 N 0.8903(3) 0.4681(3) 0.6635(2) 0.0681(11) Uani 1 1 d . . . . .
N3 N 0.7852(3) 0.3456(3) 0.79002(19) 0.0572(9) Uani 1 1 d . . . . .
N4 N 0.2332(3) 0.5747(3) 0.8712(2) 0.0690(11) Uani 1 1 d . . . . .
C1 C 0.6674(3) 1.0734(3) 0.5204(3) 0.0560(11) Uani 1 1 d . . . . .
C2 C 0.6174(4) 1.0930(3) 0.4498(3) 0.0642(12) Uani 1 1 d . . . . .
H2 H 0.545153 1.082790 0.450081 0.077 Uiso 1 1 calc R . . . .
C3 C 0.6748(4) 1.1284(4) 0.3769(3) 0.0775(14) Uani 1 1 d . . . . .
H3 H 0.642274 1.140984 0.328591 0.093 Uiso 1 1 calc R . . . .
C4 C 0.7833(4) 1.1442(4) 0.3797(3) 0.0819(16) Uani 1 1 d . . . . .
H4 H 0.823170 1.166659 0.332099 0.098 Uiso 1 1 calc R . . . .
C5 C 0.8315(4) 1.1275(4) 0.4500(3) 0.0809(16) Uani 1 1 d . . . . .
H5 H 0.903321 1.138685 0.449073 0.097 Uiso 1 1 calc R . . . .
C6 C 0.7755(4) 1.0939(4) 0.5238(3) 0.0658(12) Uani 1 1 d . . . . .
C7 C 0.8219(4) 1.0862(4) 0.5982(3) 0.0805(15) Uani 1 1 d . . . . .
H7 H 0.904652 1.061179 0.597302 0.097 Uiso 1 1 calc R . . . .
C8 C 0.7600(5) 1.1109(4) 0.6684(3) 0.0833(15) Uani 1 1 d . . . . .
H8 H 0.804768 1.104616 0.709782 0.100 Uiso 1 1 calc R . . . .
C9 C 0.6314(4) 1.1465(4) 0.6885(3) 0.0712(13) Uani 1 1 d . . . . .
C10 C 0.5752(6) 1.2232(5) 0.7466(3) 0.0967(17) Uani 1 1 d . . . . .
H10 H 0.620634 1.247317 0.774011 0.116 Uiso 1 1 calc R . . . .
C11 C 0.4524(7) 1.2623(5) 0.7626(4) 0.109(2) Uani 1 1 d . . . . .
H11 H 0.416193 1.313517 0.800551 0.130 Uiso 1 1 calc R . . . .
C12 C 0.3821(5) 1.2277(5) 0.7240(4) 0.1021(19) Uani 1 1 d . . . . .
H12 H 0.299455 1.255305 0.735379 0.122 Uiso 1 1 calc R . . . .
C13 C 0.4372(4) 1.1509(4) 0.6680(3) 0.0813(15) Uani 1 1 d . . . . .
H13 H 0.391157 1.125958 0.641656 0.098 Uiso 1 1 calc R . . . .
C14 C 0.5586(4) 1.1113(4) 0.6508(3) 0.0609(11) Uani 1 1 d . . . . .
C15 C 0.6559(3) 0.9039(3) 0.6217(2) 0.0457(9) Uani 1 1 d . . . . .
C16 C 0.7240(3) 0.8225(4) 0.5703(2) 0.0594(11) Uani 1 1 d . . . . .
H16 H 0.743376 0.850630 0.517444 0.071 Uiso 1 1 calc R . . . .
C17 C 0.7632(3) 0.7015(3) 0.5957(2) 0.0586(11) Uani 1 1 d . . . . .
H17 H 0.810163 0.649550 0.560043 0.070 Uiso 1 1 calc R . . . .
C18 C 0.7343(3) 0.6546(3) 0.6739(2) 0.0480(10) Uani 1 1 d . . . . .
C19 C 0.6673(3) 0.7361(3) 0.7263(2) 0.0547(11) Uani 1 1 d . . . . .
H19 H 0.648646 0.707627 0.779194 0.066 Uiso 1 1 calc R . . . .
C20 C 0.6281(3) 0.8582(3) 0.7013(2) 0.0526(10) Uani 1 1 d . . . . .
H20 H 0.583122 0.910394 0.737261 0.063 Uiso 1 1 calc R . . . .
C21 C 0.7846(3) 0.5248(3) 0.6999(2) 0.0514(10) Uani 1 1 d . . . . .
C22 C 0.9477(3) 0.3489(4) 0.6892(3) 0.0692(13) Uani 1 1 d . . . . .
C23 C 1.0557(4) 0.2840(5) 0.6479(3) 0.0960(18) Uani 1 1 d . . . . .
H23 H 1.087829 0.321239 0.602634 0.115 Uiso 1 1 calc R . . . .
C24 C 1.1123(4) 0.1668(5) 0.6750(4) 0.1011(19) Uani 1 1 d . . . . .
H24 H 1.182959 0.123878 0.647157 0.121 Uiso 1 1 calc R . . . .
C25 C 1.0674(4) 0.1086(4) 0.7435(3) 0.0857(16) Uani 1 1 d . . . . .
H25 H 1.110286 0.029049 0.762089 0.103 Uiso 1 1 calc R . . . .
C26 C 0.9610(4) 0.1677(4) 0.7834(3) 0.0754(14) Uani 1 1 d . . . . .
H26 H 0.930406 0.128589 0.828454 0.091 Uiso 1 1 calc R . . . .
C27 C 0.8985(3) 0.2884(3) 0.7555(3) 0.0582(11) Uani 1 1 d . . . . .
C28 C 0.7275(3) 0.4578(3) 0.7626(2) 0.0476(9) Uani 1 1 d . . . . .
C29 C 0.5985(3) 0.5057(3) 0.7921(2) 0.0485(10) Uani 1 1 d . . . . .
C30 C 0.5628(3) 0.4705(3) 0.8718(2) 0.0552(11) Uani 1 1 d . . . . .
H30 H 0.620912 0.428253 0.907260 0.066 Uiso 1 1 calc R . . . .
C31 C 0.4442(3) 0.4967(3) 0.8990(2) 0.0580(11) Uani 1 1 d . . . . .
H31 H 0.423271 0.475048 0.952850 0.070 Uiso 1 1 calc R . . . .
C32 C 0.3550(3) 0.5557(3) 0.8465(2) 0.0518(10) Uani 1 1 d . . . . .
C33 C 0.3881(3) 0.5962(3) 0.7666(2) 0.0538(11) Uani 1 1 d . . . . .
H33 H 0.330173 0.639527 0.731164 0.065 Uiso 1 1 calc R . . . .
C34 C 0.5094(3) 0.5701(3) 0.7416(2) 0.0522(10) Uani 1 1 d . . . . .
H34 H 0.530975 0.597062 0.688999 0.063 Uiso 1 1 calc R . . . .
C35 C 0.1396(3) 0.6374(4) 0.8192(3) 0.0617(12) Uani 1 1 d . . . . .
C36 C 0.1314(4) 0.5880(5) 0.7550(3) 0.0742(14) Uani 1 1 d . . . . .
H36 H 0.186206 0.513034 0.745908 0.089 Uiso 1 1 calc R . . . .
C37 C 0.0408(5) 0.6504(6) 0.7033(3) 0.0876(16) Uani 1 1 d . . . . .
H37 H 0.033397 0.616868 0.660817 0.105 Uiso 1 1 calc R . . . .
C38 C -0.0370(4) 0.7628(6) 0.7172(4) 0.0913(18) Uani 1 1 d . . . . .
H38 H -0.095650 0.806552 0.682388 0.110 Uiso 1 1 calc R . . . .
C39 C -0.0293(4) 0.8105(5) 0.7807(4) 0.0861(17) Uani 1 1 d . . . . .
H39 H -0.083976 0.886178 0.788312 0.103 Uiso 1 1 calc R . . . .
C40 C 0.0581(4) 0.7503(4) 0.8360(3) 0.0725(14) Uani 1 1 d . . . . .
C41 C 0.0548(4) 0.8010(5) 0.9077(4) 0.0933(17) Uani 1 1 d . . . . .
H41 H 0.031238 0.883634 0.902616 0.112 Uiso 1 1 calc R . . . .
C42 C 0.0830(4) 0.7381(5) 0.9807(3) 0.0911(16) Uani 1 1 d . . . . .
H42 H 0.074307 0.782841 1.021136 0.109 Uiso 1 1 calc R . . . .
C43 C 0.1250(4) 0.6103(5) 1.0037(3) 0.0716(13) Uani 1 1 d . . . . .
C44 C 0.0918(4) 0.5599(6) 1.0812(3) 0.0884(17) Uani 1 1 d . . . . .
H44 H 0.044848 0.610156 1.117775 0.106 Uiso 1 1 calc R . . . .
C45 C 0.1276(5) 0.4385(7) 1.1033(3) 0.103(2) Uani 1 1 d . . . . .
H45 H 0.106177 0.408581 1.155298 0.124 Uiso 1 1 calc R . . . .
C46 C 0.1949(5) 0.3586(5) 1.0505(3) 0.0968(18) Uani 1 1 d . . . . .
H46 H 0.217120 0.276453 1.066111 0.116 Uiso 1 1 calc R . . . .
C47 C 0.2282(4) 0.4062(5) 0.9726(3) 0.0814(15) Uani 1 1 d . . . . .
H47 H 0.272768 0.354979 0.935874 0.098 Uiso 1 1 calc R . . . .
C48 C 0.1947(3) 0.5297(4) 0.9501(2) 0.0628(12) 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
N1 C1 1.457(4) . ?
N1 C14 1.435(5) . ?
N1 C15 1.406(4) . ?
N2 C21 1.325(4) . ?
N2 C22 1.370(5) . ?
N3 C27 1.380(4) . ?
N3 C28 1.310(4) . ?
N4 C32 1.414(4) . ?
N4 C35 1.433(5) . ?
N4 C48 1.433(4) . ?
C1 C2 1.373(6) . ?
C1 C6 1.437(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.406(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.411(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.361(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(6) . ?
C6 C7 1.439(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.334(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.455(6) . ?
C9 C10 1.410(6) . ?
C9 C14 1.396(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(5) . ?
C15 C16 1.389(5) . ?
C15 C20 1.408(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(5) . ?
C18 C19 1.398(5) . ?
C18 C21 1.471(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(5) . ?
C20 H20 0.9300 . ?
C21 C28 1.472(5) . ?
C22 C23 1.409(5) . ?
C22 C27 1.411(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.353(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.398(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.364(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.404(5) . ?
C28 C29 1.491(4) . ?
C29 C30 1.400(5) . ?
C29 C34 1.382(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.375(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.397(5) . ?
C32 C33 1.412(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.397(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(6) . ?
C35 C40 1.411(6) . ?
C36 H36 0.9300 . ?
C36 C37 1.403(6) . ?
C37 H37 0.9300 . ?
C37 C38 1.380(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.355(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.416(7) . ?
C40 C41 1.463(7) . ?
C41 H41 0.9300 . ?
C41 C42 1.350(7) . ?
C42 H42 0.9300 . ?
C42 C43 1.441(7) . ?
C43 C44 1.416(6) . ?
C43 C48 1.413(6) . ?
C44 H44 0.9300 . ?
C44 C45 1.371(7) . ?
C45 H45 0.9300 . ?
C45 C46 1.393(8) . ?
C46 H46 0.9300 . ?
C46 C47 1.411(6) . ?
C47 H47 0.9300 . ?
C47 C48 1.397(6) . ?

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
C14 N1 C1 114.8(3) . . ?
C15 N1 C1 118.9(3) . . ?
C15 N1 C14 120.7(3) . . ?
C21 N2 C22 118.7(3) . . ?
C28 N3 C27 118.8(3) . . ?
C32 N4 C35 122.9(3) . . ?
C32 N4 C48 122.1(3) . . ?
C35 N4 C48 114.9(3) . . ?
C2 C1 N1 120.1(3) . . ?
C2 C1 C6 122.0(4) . . ?
C6 C1 N1 117.8(4) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.7(5) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 121.9(4) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.7(4) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 122.6(4) . . ?
C5 C6 C1 116.1(5) . . ?
C5 C6 C7 121.2(4) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 C6 127.5(4) . . ?
C8 C7 H7 116.2 . . ?
C7 C8 H8 115.8 . . ?
C7 C8 C9 128.4(5) . . ?
C9 C8 H8 115.8 . . ?
C10 C9 C8 119.6(5) . . ?
C14 C9 C8 122.9(5) . . ?
C14 C9 C10 117.4(5) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.7(6) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.0(5) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 120.8 . . ?
C11 C12 C13 118.4(5) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 N1 119.3(4) . . ?
C13 C14 N1 118.9(4) . . ?
C13 C14 C9 121.8(4) . . ?
N1 C15 C20 120.8(3) . . ?
C16 C15 N1 121.4(3) . . ?
C16 C15 C20 117.8(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.5(4) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C19 117.2(3) . . ?
C17 C18 C21 119.5(3) . . ?
C19 C18 C21 122.9(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.6(3) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
N2 C21 C18 115.3(3) . . ?
N2 C21 C28 119.8(3) . . ?
C18 C21 C28 124.9(3) . . ?
N2 C22 C23 120.0(4) . . ?
N2 C22 C27 121.0(3) . . ?
C23 C22 C27 118.9(4) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.2(4) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 119.1 . . ?
C23 C24 C25 121.8(4) . . ?
C25 C24 H24 119.1 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.5(5) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.5 . . ?
C25 C26 C27 119.0(4) . . ?
C27 C26 H26 120.5 . . ?
N3 C27 C22 120.0(4) . . ?
N3 C27 C26 119.5(4) . . ?
C26 C27 C22 120.3(4) . . ?
N3 C28 C21 121.0(3) . . ?
N3 C28 C29 115.1(3) . . ?
C21 C28 C29 123.4(3) . . ?
C30 C29 C28 119.3(4) . . ?
C34 C29 C28 122.7(3) . . ?
C34 C29 C30 117.3(3) . . ?
C29 C30 H30 119.1 . . ?
C31 C30 C29 121.9(4) . . ?
C31 C30 H30 119.1 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.5(3) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 N4 121.8(3) . . ?
C31 C32 C33 118.7(3) . . ?
C33 C32 N4 119.5(4) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 C32 118.9(4) . . ?
C34 C33 H33 120.6 . . ?
C29 C34 C33 122.6(3) . . ?
C29 C34 H34 118.7 . . ?
C33 C34 H34 118.7 . . ?
C36 C35 N4 120.4(4) . . ?
C36 C35 C40 122.1(5) . . ?
C40 C35 N4 117.5(5) . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.3(5) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 120.8 . . ?
C38 C37 C36 118.4(6) . . ?
C38 C37 H37 120.8 . . ?
C37 C38 H38 119.4 . . ?
C39 C38 C37 121.2(6) . . ?
C39 C38 H38 119.4 . . ?
C38 C39 H39 118.5 . . ?
C38 C39 C40 122.9(6) . . ?
C40 C39 H39 118.5 . . ?
C35 C40 C39 115.1(5) . . ?
C35 C40 C41 124.3(5) . . ?
C39 C40 C41 120.5(5) . . ?
C40 C41 H41 117.2 . . ?
C42 C41 C40 125.6(5) . . ?
C42 C41 H41 117.2 . . ?
C41 C42 H42 116.0 . . ?
C41 C42 C43 128.1(5) . . ?
C43 C42 H42 116.0 . . ?
C44 C43 C42 120.5(5) . . ?
C48 C43 C42 122.6(4) . . ?
C48 C43 C44 116.9(5) . . ?
C43 C44 H44 119.3 . . ?
C45 C44 C43 121.4(5) . . ?
C45 C44 H44 119.3 . . ?
C44 C45 H45 119.0 . . ?
C44 C45 C46 122.0(5) . . ?
C46 C45 H45 119.0 . . ?
C45 C46 H46 121.1 . . ?
C45 C46 C47 117.9(6) . . ?
C47 C46 H46 121.1 . . ?
C46 C47 H47 119.8 . . ?
C48 C47 C46 120.5(5) . . ?
C48 C47 H47 119.8 . . ?
C43 C48 N4 119.7(4) . . ?
C47 C48 N4 118.9(4) . . ?
C47 C48 C43 121.3(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.296 0.000 0.000 486.7 149.8 ?
2 -0.190 0.500 0.500 303.8 99.2 ?

_olex2_exptl_crystal_mounting_method 'crystal was mounted using loop with glue'
_olex2_submission_original_sample_id ISB_2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.152
_oxdiff_exptl_absorpt_empirical_full_min 0.547
