# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_zhaoqsh_0401
_database_code_depnum_ccdc_archive 'CCDC 1950969'
loop_
_audit_author_name
_audit_author_address
'Quan-Sheng Zhao'
;CCDC
China
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;
_audit_creation_date             2019-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 Br N O2'
_chemical_formula_sum            'C24 H26 Br N O2'
_chemical_formula_weight         440.37
_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 0.0181 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'

_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                   8.8862(4)
_cell_length_b                   9.2731(5)
_cell_length_c                   14.1317(6)
_cell_angle_alpha                90.728(4)
_cell_angle_beta                 101.126(4)
_cell_angle_gamma                116.691(5)
_cell_volume                     1014.26(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3950
_cell_measurement_temperature    291.19(19)
_cell_measurement_theta_max      69.6840
_cell_measurement_theta_min      6.2530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6463
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         5.374
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.19(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  111.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega   63.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega   51.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega   52.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -73.0000    3.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   43.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   55.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega   49.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega  -11.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 13 omega   33.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
 14 omega  101.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000  132.0000 76

#__ type_ start__ end____ width___ exp.time_
 15 omega  106.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega   97.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   89.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
 18 omega   84.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
 19 omega   88.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
 20 omega   46.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   42.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
 22 omega   47.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   46.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 24 omega   24.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 25 omega  -10.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -73.0000    3.0000 42

#__ type_ start__ end____ width___ exp.time_
 26 omega  -26.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 27 omega  -60.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1143186000
_diffrn_orient_matrix_UB_12      0.1630130000
_diffrn_orient_matrix_UB_13      -0.0339066000
_diffrn_orient_matrix_UB_21      -0.1511235000
_diffrn_orient_matrix_UB_22      -0.0257015000
_diffrn_orient_matrix_UB_23      -0.0845321000
_diffrn_orient_matrix_UB_31      -0.0608668000
_diffrn_orient_matrix_UB_32      0.0882770000
_diffrn_orient_matrix_UB_33      0.0648793000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3380
_reflns_number_total             3573
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.608
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+0.8411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C4(H4A,H4B), C7(H7A,H7B), C0AA(H0AA,H0AB), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C3AA(H3AA), C4AA(H4AA), C20(H20), C24(H24), C1(H1), C7AA(H7AA),
 C8(H8), C1AA(H1AA), C2AA(H2AA)
2.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br2 Br 0.47726(5) 0.46686(5) 0.26239(2) 0.05964(15) Uani 1 1 d . . . . .
N2 N 0.2055(2) 0.7215(2) 0.41200(13) 0.0281(4) Uani 1 1 d . . . . .
O6AA O -0.0093(3) 0.7743(3) 0.32539(15) 0.0593(6) Uani 1 1 d . . . . .
O6 O -0.0119(4) 0.7179(3) -0.02589(15) 0.0695(7) Uani 1 1 d . . . . .
C10 C 0.2775(3) 0.6082(3) 0.40080(15) 0.0259(4) Uani 1 1 d . . . . .
H10 H 0.403838 0.667718 0.419968 0.031 Uiso 1 1 calc R . . . .
C11 C 0.2300(3) 0.4040(3) 0.26006(18) 0.0355(5) Uani 1 1 d . . . . .
H11 H 0.161770 0.362090 0.193585 0.043 Uiso 1 1 calc R . . . .
C14 C 0.2126(3) 0.4674(3) 0.46264(17) 0.0338(5) Uani 1 1 d . . . . .
H14A H 0.268017 0.506782 0.530420 0.041 Uiso 1 1 calc R . . . .
H14B H 0.088990 0.424962 0.455876 0.041 Uiso 1 1 calc R . . . .
C15 C 0.2612(3) 0.8267(3) 0.49973(16) 0.0275(5) Uani 1 1 d . . . . .
C17 C 0.2231(3) 0.5592(3) 0.29068(15) 0.0267(5) Uani 1 1 d . . . . .
H17 H 0.308455 0.646543 0.262675 0.032 Uiso 1 1 calc R . . . .
C5AA C -0.1131(3) 0.4144(4) 0.2638(2) 0.0475(7) Uani 1 1 d . . . . .
H5AA H -0.131010 0.329040 0.217088 0.071 Uiso 1 1 calc GR . . . .
H5AB H -0.210343 0.436565 0.250232 0.071 Uiso 1 1 calc GR . . . .
H5AC H -0.100967 0.381395 0.327795 0.071 Uiso 1 1 calc GR . . . .
C4 C 0.2515(4) 0.3319(3) 0.43156(19) 0.0408(6) Uani 1 1 d . . . . .
H4A H 0.375594 0.372475 0.442443 0.049 Uiso 1 1 calc R . . . .
H4B H 0.207262 0.243324 0.470706 0.049 Uiso 1 1 calc R . . . .
C5 C 0.0521(3) 0.5689(3) 0.25801(17) 0.0319(5) Uani 1 1 d . . . . .
C7 C 0.1697(4) 0.2695(3) 0.3249(2) 0.0444(6) Uani 1 1 d . . . . .
H7A H 0.198968 0.185689 0.306692 0.053 Uiso 1 1 calc R . . . .
H7B H 0.045038 0.221127 0.315282 0.053 Uiso 1 1 calc R . . . .
C0AA C 0.0245(4) 0.6162(3) 0.15442(18) 0.0387(6) Uani 1 1 d . . . . .
H0AA H 0.019373 0.532707 0.109962 0.046 Uiso 1 1 calc R . . . .
H0AB H -0.087285 0.614974 0.138986 0.046 Uiso 1 1 calc R . . . .
C12 C 0.4039(3) 0.8414(3) 0.56841(18) 0.0373(5) Uani 1 1 d . . . . .
H12 H 0.462386 0.784078 0.555926 0.045 Uiso 1 1 calc R . . . .
C13 C 0.0761(3) 0.7014(3) 0.33399(17) 0.0346(5) Uani 1 1 d . . . . .
C3AA C 0.4597(4) 0.9401(3) 0.65499(19) 0.0422(6) Uani 1 1 d . . . . .
H3AA H 0.554796 0.947929 0.700376 0.051 Uiso 1 1 calc R . . . .
C4AA C 0.1780(3) 0.9161(3) 0.51933(19) 0.0361(5) Uani 1 1 d . . . . .
H4AA H 0.083593 0.909867 0.474071 0.043 Uiso 1 1 calc R . . . .
C20 C 0.3760(4) 1.0270(3) 0.67460(19) 0.0415(6) Uani 1 1 d . . . . .
H20 H 0.413409 1.093033 0.732985 0.050 Uiso 1 1 calc R . . . .
C21 C 0.1134(4) 0.8166(4) 0.03198(18) 0.0470(7) Uani 1 1 d . . . . .
C24 C 0.4895(7) 1.2320(6) 0.0310(3) 0.0941(16) Uani 1 1 d . . . . .
H24 H 0.597842 1.301306 0.069172 0.113 Uiso 1 1 calc R . . . .
C1 C 0.4287(7) 1.2750(5) -0.0557(3) 0.0792(12) Uani 1 1 d . . . . .
H1 H 0.494948 1.375406 -0.075079 0.095 Uiso 1 1 calc R . . . .
C7AA C 0.2727(6) 1.1719(5) -0.1132(2) 0.0674(10) Uani 1 1 d . . . . .
H7AA H 0.234438 1.200921 -0.172311 0.081 Uiso 1 1 calc R . . . .
C8AA C 0.2278(5) 0.9783(4) 0.00428(19) 0.0492(7) Uani 1 1 d . . . . .
C8 C 0.2366(4) 1.0147(3) 0.6069(2) 0.0415(6) Uani 1 1 d . . . . .
H8 H 0.179910 1.073654 0.619757 0.050 Uiso 1 1 calc R . . . .
C9 C 0.1580(4) 0.7789(4) 0.13480(18) 0.0469(7) Uani 1 1 d . . . . .
H9A H 0.269405 0.779492 0.145781 0.056 Uiso 1 1 calc R . . . .
H9B H 0.167541 0.863546 0.180217 0.056 Uiso 1 1 calc R . . . .
C1AA C 0.1709(5) 1.0240(4) -0.0840(2) 0.0561(8) Uani 1 1 d . . . . .
H1AA H 0.063969 0.954465 -0.123442 0.067 Uiso 1 1 calc R . . . .
C2AA C 0.3871(6) 1.0843(5) 0.0606(2) 0.0761(12) Uani 1 1 d . . . . .
H2AA H 0.426798 1.056134 0.119731 0.091 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C11 1.997(3) . ?
N2 C10 1.475(3) . ?
N2 C15 1.426(3) . ?
N2 C13 1.373(3) . ?
O6AA C13 1.215(3) . ?
O6 C21 1.208(4) . ?
C10 H10 0.9800 . ?
C10 C14 1.532(3) . ?
C10 C17 1.535(3) . ?
C11 H11 0.9800 . ?
C11 C17 1.528(3) . ?
C11 C7 1.517(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C4 1.525(3) . ?
C15 C12 1.391(3) . ?
C15 C4AA 1.390(3) . ?
C17 H17 0.9800 . ?
C17 C5 1.544(3) . ?
C5AA H5AA 0.9600 . ?
C5AA H5AB 0.9600 . ?
C5AA H5AC 0.9600 . ?
C5AA C5 1.541(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C7 1.520(4) . ?
C5 C0AA 1.539(3) . ?
C5 C13 1.533(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?
C0AA C9 1.513(4) . ?
C12 H12 0.9300 . ?
C12 C3AA 1.382(4) . ?
C3AA H3AA 0.9300 . ?
C3AA C20 1.376(4) . ?
C4AA H4AA 0.9300 . ?
C4AA C8 1.391(4) . ?
C20 H20 0.9300 . ?
C20 C8 1.370(4) . ?
C21 C8AA 1.494(4) . ?
C21 C9 1.518(3) . ?
C24 H24 0.9300 . ?
C24 C1 1.380(6) . ?
C24 C2AA 1.386(6) . ?
C1 H1 0.9300 . ?
C1 C7AA 1.360(6) . ?
C7AA H7AA 0.9300 . ?
C7AA C1AA 1.383(5) . ?
C8AA C1AA 1.398(4) . ?
C8AA C2AA 1.379(5) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C1AA H1AA 0.9300 . ?
C2AA H2AA 0.9300 . ?

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
C15 N2 C10 120.62(18) . . ?
C13 N2 C10 112.30(18) . . ?
C13 N2 C15 126.87(19) . . ?
N2 C10 H10 109.1 . . ?
N2 C10 C14 112.11(18) . . ?
N2 C10 C17 102.04(17) . . ?
C14 C10 H10 109.1 . . ?
C14 C10 C17 115.19(19) . . ?
C17 C10 H10 109.1 . . ?
Br2 C11 H11 109.0 . . ?
C17 C11 Br2 106.63(16) . . ?
C17 C11 H11 109.0 . . ?
C7 C11 Br2 107.17(18) . . ?
C7 C11 H11 109.0 . . ?
C7 C11 C17 115.7(2) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C4 C14 C10 110.9(2) . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C12 C15 N2 119.2(2) . . ?
C4AA C15 N2 122.3(2) . . ?
C4AA C15 C12 118.5(2) . . ?
C10 C17 H17 106.1 . . ?
C10 C17 C5 105.20(18) . . ?
C11 C17 C10 113.75(18) . . ?
C11 C17 H17 106.1 . . ?
C11 C17 C5 118.83(19) . . ?
C5 C17 H17 106.1 . . ?
H5AA C5AA H5AB 109.5 . . ?
H5AA C5AA H5AC 109.5 . . ?
H5AB C5AA H5AC 109.5 . . ?
C5 C5AA H5AA 109.5 . . ?
C5 C5AA H5AB 109.5 . . ?
C5 C5AA H5AC 109.5 . . ?
C14 C4 H4A 109.5 . . ?
C14 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C7 C4 C14 110.9(2) . . ?
C7 C4 H4A 109.5 . . ?
C7 C4 H4B 109.5 . . ?
C5AA C5 C17 115.7(2) . . ?
C0AA C5 C17 113.5(2) . . ?
C0AA C5 C5AA 107.1(2) . . ?
C13 C5 C17 101.20(18) . . ?
C13 C5 C5AA 107.7(2) . . ?
C13 C5 C0AA 111.5(2) . . ?
C11 C7 C4 111.9(2) . . ?
C11 C7 H7A 109.2 . . ?
C11 C7 H7B 109.2 . . ?
C4 C7 H7A 109.2 . . ?
C4 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C5 C0AA H0AA 108.0 . . ?
C5 C0AA H0AB 108.0 . . ?
H0AA C0AA H0AB 107.3 . . ?
C9 C0AA C5 117.1(2) . . ?
C9 C0AA H0AA 108.0 . . ?
C9 C0AA H0AB 108.0 . . ?
C15 C12 H12 119.6 . . ?
C3AA C12 C15 120.8(2) . . ?
C3AA C12 H12 119.6 . . ?
N2 C13 C5 109.50(19) . . ?
O6AA C13 N2 126.3(2) . . ?
O6AA C13 C5 124.2(2) . . ?
C12 C3AA H3AA 119.7 . . ?
C20 C3AA C12 120.6(3) . . ?
C20 C3AA H3AA 119.7 . . ?
C15 C4AA H4AA 120.1 . . ?
C15 C4AA C8 119.7(2) . . ?
C8 C4AA H4AA 120.1 . . ?
C3AA C20 H20 120.5 . . ?
C8 C20 C3AA 119.1(2) . . ?
C8 C20 H20 120.5 . . ?
O6 C21 C8AA 121.0(3) . . ?
O6 C21 C9 120.6(3) . . ?
C8AA C21 C9 118.5(2) . . ?
C1 C24 H24 120.4 . . ?
C1 C24 C2AA 119.1(4) . . ?
C2AA C24 H24 120.4 . . ?
C24 C1 H1 119.7 . . ?
C7AA C1 C24 120.6(4) . . ?
C7AA C1 H1 119.7 . . ?
C1 C7AA H7AA 119.9 . . ?
C1 C7AA C1AA 120.3(3) . . ?
C1AA C7AA H7AA 119.9 . . ?
C1AA C8AA C21 118.3(3) . . ?
C2AA C8AA C21 123.6(3) . . ?
C2AA C8AA C1AA 118.1(3) . . ?
C4AA C8 H8 119.3 . . ?
C20 C8 C4AA 121.4(2) . . ?
C20 C8 H8 119.3 . . ?
C0AA C9 C21 112.6(2) . . ?
C0AA C9 H9A 109.1 . . ?
C0AA C9 H9B 109.1 . . ?
C21 C9 H9A 109.1 . . ?
C21 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C7AA C1AA C8AA 120.4(3) . . ?
C7AA C1AA H1AA 119.8 . . ?
C8AA C1AA H1AA 119.8 . . ?
C24 C2AA H2AA 119.3 . . ?
C8AA C2AA C24 121.4(3) . . ?
C8AA C2AA H2AA 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br2 C11 C17 C10 -79.7(2) . . . . ?
Br2 C11 C17 C5 155.65(17) . . . . ?
Br2 C11 C7 C4 70.4(2) . . . . ?
N2 C10 C14 C4 166.0(2) . . . . ?
N2 C10 C17 C11 -161.98(19) . . . . ?
N2 C10 C17 C5 -30.3(2) . . . . ?
N2 C15 C12 C3AA -178.9(2) . . . . ?
N2 C15 C4AA C8 179.0(2) . . . . ?
O6 C21 C8AA C1AA 10.9(5) . . . . ?
O6 C21 C8AA C2AA -168.4(4) . . . . ?
O6 C21 C9 C0AA -3.9(4) . . . . ?
C10 N2 C15 C12 10.6(3) . . . . ?
C10 N2 C15 C4AA -169.5(2) . . . . ?
C10 N2 C13 O6AA 177.4(3) . . . . ?
C10 N2 C13 C5 -1.7(3) . . . . ?
C10 C14 C4 C7 -57.9(3) . . . . ?
C10 C17 C5 C5AA -87.0(2) . . . . ?
C10 C17 C5 C0AA 148.64(19) . . . . ?
C10 C17 C5 C13 29.0(2) . . . . ?
C11 C17 C5 C5AA 41.7(3) . . . . ?
C11 C17 C5 C0AA -82.6(3) . . . . ?
C11 C17 C5 C13 157.8(2) . . . . ?
C14 C10 C17 C11 -40.3(3) . . . . ?
C14 C10 C17 C5 91.5(2) . . . . ?
C14 C4 C7 C11 57.4(3) . . . . ?
C15 N2 C10 C14 71.6(3) . . . . ?
C15 N2 C10 C17 -164.60(19) . . . . ?
C15 N2 C13 O6AA 2.6(4) . . . . ?
C15 N2 C13 C5 -176.6(2) . . . . ?
C15 C12 C3AA C20 -0.5(4) . . . . ?
C15 C4AA C8 C20 0.4(4) . . . . ?
C17 C10 C14 C4 49.9(3) . . . . ?
C17 C11 C7 C4 -48.4(3) . . . . ?
C17 C5 C0AA C9 -60.2(3) . . . . ?
C17 C5 C13 N2 -17.4(3) . . . . ?
C17 C5 C13 O6AA 163.5(3) . . . . ?
C5AA C5 C0AA C9 170.9(2) . . . . ?
C5AA C5 C13 N2 104.4(2) . . . . ?
C5AA C5 C13 O6AA -74.7(3) . . . . ?
C5 C0AA C9 C21 -177.2(2) . . . . ?
C7 C11 C17 C10 39.4(3) . . . . ?
C7 C11 C17 C5 -85.3(3) . . . . ?
C0AA C5 C13 N2 -138.4(2) . . . . ?
C0AA C5 C13 O6AA 42.4(4) . . . . ?
C12 C15 C4AA C8 -1.2(4) . . . . ?
C12 C3AA C20 C8 -0.2(4) . . . . ?
C13 N2 C10 C14 -103.6(2) . . . . ?
C13 N2 C10 C17 20.2(2) . . . . ?
C13 N2 C15 C12 -175.0(2) . . . . ?
C13 N2 C15 C4AA 4.9(4) . . . . ?
C13 C5 C0AA C9 53.3(3) . . . . ?
C3AA C20 C8 C4AA 0.3(4) . . . . ?
C4AA C15 C12 C3AA 1.2(4) . . . . ?
C21 C8AA C1AA C7AA -179.5(3) . . . . ?
C21 C8AA C2AA C24 179.1(4) . . . . ?
C24 C1 C7AA C1AA 1.7(6) . . . . ?
C1 C24 C2AA C8AA 1.4(8) . . . . ?
C1 C7AA C1AA C8AA -0.6(5) . . . . ?
C8AA C21 C9 C0AA 176.0(3) . . . . ?
C9 C21 C8AA C1AA -169.0(3) . . . . ?
C9 C21 C8AA C2AA 11.7(5) . . . . ?
C1AA C8AA C2AA C24 -0.3(6) . . . . ?
C2AA C24 C1 C7AA -2.1(8) . . . . ?
C2AA C8AA C1AA C7AA -0.1(5) . . . . ?

_olex2_date_sample_data_collection 2019-04-03
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zhaoqsh_0603
_database_code_depnum_ccdc_archive 'CCDC 1950971'
loop_
_audit_author_name
_audit_author_address
'Quan-Sheng Zhao'
;CCDC
China
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;
_audit_creation_date             2019-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 Cl N O2'
_chemical_formula_sum            'C24 H26 Cl N O2'
_chemical_formula_weight         395.91
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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      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                   8.7322(5)
_cell_length_b                   9.3453(4)
_cell_length_c                   13.9189(7)
_cell_angle_alpha                90.640(4)
_cell_angle_beta                 99.884(4)
_cell_angle_gamma                116.102(5)
_cell_volume                     1000.04(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    291.96(10)
_cell_measurement_theta_max      69.9660
_cell_measurement_theta_min      8.2340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6168
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         5.296
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.96(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00 124.00   1.00    1.00    --   54.00   0.00   0.00  137
  2  ω     96.00 178.00   1.00    1.00    --  108.00  25.00 -60.00   82
  3  ω    133.00 175.00   1.00    1.00    --  108.00  50.00   0.00   42
  4  ω     94.00 124.00   1.00    1.00    --  108.00 -50.00  90.00   30
  5  ω     78.00 137.00   1.00    1.00    --  108.00 -91.00  90.00   59
  6  ω     75.00 111.00   1.00    1.00    --  108.00-111.00  60.00   36
  7  ω     76.00 104.00   1.00    1.00    --  108.00-111.00 -30.00   28
  8  ω     52.00  88.00   1.00    1.00    --   54.00-125.00-120.00   36
  9  ω     39.00  65.00   1.00    1.00    --  108.00-111.00 -30.00   26
 10  ω     36.00  81.00   1.00    1.00    --  108.00-111.00  30.00   45
 11  ω     42.00 127.00   1.00    1.00    --  108.00 -63.00   0.00   85
 12  ω     63.00 126.00   1.00    1.00    --  108.00 -25.00-120.00   63
 13  ω     80.00 114.00   1.00    1.00    --  108.00-111.00-150.00   34
 14  ω     40.00 126.00   1.00    1.00    --  108.00 -63.00-150.00   86
 15  ω     40.00  74.00   1.00    1.00    --  108.00 -25.00-180.00   34
 16  ω     28.00 124.00   1.00    1.00    --   54.00  77.00-180.00   96
 17  ω     59.00  97.00   1.00    1.00    --  108.00 178.00 -90.00   38
 18  ω     29.00  64.00   1.00    1.00    --    0.00  77.00  60.00   35
 19  ω    -30.00  17.00   1.00    1.00    --    0.00  77.00  60.00   47
 20  ω     39.00  90.00   1.00    1.00    --  108.00 -50.00  90.00   51
 21  ω     36.00 135.00   1.00    1.00    --  108.00 -25.00 -30.00   99
 22  ω     24.00  55.00   1.00    1.00    --   54.00-125.00  90.00   31
 23  ω     23.00 108.00   1.00    1.00    --   54.00-125.00 150.00   85
 24  ω     23.00  61.00   1.00    1.00    --   54.00-125.00  30.00   38
 25  ω     -7.00  51.00   1.00    1.00    --   54.00 -57.00-120.00   58
 26  ω    -72.00 -26.00   1.00    1.00    --    0.00 -38.00 -60.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1643976000
_diffrn_orient_matrix_UB_12      -0.0406700000
_diffrn_orient_matrix_UB_13      0.0425703000
_diffrn_orient_matrix_UB_21      -0.1135950000
_diffrn_orient_matrix_UB_22      -0.1059778000
_diffrn_orient_matrix_UB_23      -0.0951272000
_diffrn_orient_matrix_UB_31      0.0147579000
_diffrn_orient_matrix_UB_32      -0.1453930000
_diffrn_orient_matrix_UB_33      0.0433964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3266
_reflns_number_total             3532
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.078
_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)+(0.0719P)²+0.2774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1248
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C11(H11), C14(H14), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.03175(7) 0.53765(7) 0.24005(4) 0.05750(19) Uani 1 1 d . . . . .
N1 N 0.29182(17) 0.27904(15) 0.08873(9) 0.0279(3) Uani 1 1 d . . . . .
C2 C 0.23773(19) 0.17540(17) 0.00103(11) 0.0267(3) Uani 1 1 d . . . . .
O3 O 0.5078(2) 0.2246(2) 0.17497(10) 0.0578(4) Uani 1 1 d . . . . .
C4 C 0.26986(19) 0.43885(17) 0.21138(11) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.182927 0.352766 0.240315 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3220(2) 0.08528(19) -0.01921(12) 0.0350(4) Uani 1 1 d . . . . .
H5 H 0.416573 0.090235 0.025848 0.042 Uiso 1 1 calc R . . . .
C6 C 0.4205(2) 0.2976(2) 0.16688(12) 0.0340(4) Uani 1 1 d . . . . .
C7 C 0.21830(19) 0.39177(17) 0.10030(11) 0.0257(3) Uani 1 1 d . . . . .
H7 H 0.091256 0.334174 0.081656 0.031 Uiso 1 1 calc R . . . .
C8 C 0.0946(2) 0.1627(2) -0.06763(12) 0.0369(4) Uani 1 1 d . . . . .
H8 H 0.035577 0.220599 -0.054907 0.044 Uiso 1 1 calc R . . . .
C9 C 0.0397(2) 0.0653(2) -0.15416(13) 0.0423(4) Uani 1 1 d . . . . .
H9 H -0.055897 0.058314 -0.199133 0.051 Uiso 1 1 calc R . . . .
O10 O 0.4954(3) 0.27182(19) 0.53013(11) 0.0702(5) Uani 1 1 d . . . . .
C11 C 0.1249(2) -0.0218(2) -0.17474(13) 0.0406(4) Uani 1 1 d . . . . .
H11 H 0.088732 -0.086251 -0.233535 0.049 Uiso 1 1 calc R . . . .
C12 C 0.2614(2) 0.5921(2) 0.24215(12) 0.0362(4) Uani 1 1 d . . . . .
H12 H 0.327750 0.632239 0.309097 0.043 Uiso 1 1 calc R . . . .
C13 C 0.4664(2) 0.3782(2) 0.34837(12) 0.0383(4) Uani 1 1 d . . . . .
H13A H 0.580694 0.381637 0.364352 0.046 Uiso 1 1 calc R . . . .
H13B H 0.465672 0.457936 0.393203 0.046 Uiso 1 1 calc R . . . .
C14 C 0.2647(2) -0.0117(2) -0.10658(14) 0.0406(4) Uani 1 1 d . . . . .
H14 H 0.321844 -0.071255 -0.119532 0.049 Uiso 1 1 calc R . . . .
C15 C 0.2852(2) 0.5314(2) 0.03711(12) 0.0335(4) Uani 1 1 d . . . . .
H15A H 0.235(3) 0.497(2) -0.0309(16) 0.040 Uiso 1 1 d R . . . .
C16 C 0.2638(3) 0.0120(2) 0.49807(13) 0.0464(5) Uani 1 1 d . . . . .
C17 C 0.3243(3) 0.7254(2) 0.17574(14) 0.0442(4) Uani 1 1 d . . . . .
H17A H 0.450013 0.771691 0.184802 0.053 Uiso 1 1 calc R . . . .
H17B H 0.294282 0.808828 0.194053 0.053 Uiso 1 1 calc R . . . .
C18 C 0.3750(3) 0.1745(2) 0.47102(12) 0.0456(5) Uani 1 1 d . . . . .
C19 C 0.2449(3) 0.6653(2) 0.06853(14) 0.0405(4) Uani 1 1 d . . . . .
H19A H 0.290486 0.753032 0.028471 0.049 Uiso 1 1 calc R . . . .
H19B H 0.119851 0.626451 0.058288 0.049 Uiso 1 1 calc R . . . .
C20 C 0.4421(2) 0.42737(19) 0.24377(11) 0.0312(4) Uani 1 1 d . . . . .
C21 C 0.3340(3) 0.2149(2) 0.36749(13) 0.0459(5) Uani 1 1 d . . . . .
H21A H 0.329969 0.134064 0.321436 0.055 Uiso 1 1 calc R . . . .
H21B H 0.219872 0.212079 0.356133 0.055 Uiso 1 1 calc R . . . .
C22 C 0.6094(2) 0.5790(2) 0.23723(15) 0.0454(4) Uani 1 1 d . . . . .
H22A H 0.597734 0.615209 0.173349 0.068 Uiso 1 1 calc GR . . . .
H22B H 0.706628 0.554686 0.248271 0.068 Uiso 1 1 calc GR . . . .
H22C H 0.628020 0.661462 0.286008 0.068 Uiso 1 1 calc GR . . . .
C23 C 0.2204(4) -0.1834(3) 0.61549(16) 0.0631(6) Uani 1 1 d . . . . .
H23 H 0.258453 -0.213415 0.674846 0.076 Uiso 1 1 calc R . . . .
C24 C 0.3193(3) -0.0349(3) 0.58706(14) 0.0538(5) Uani 1 1 d . . . . .
H24 H 0.423809 0.034671 0.627456 0.065 Uiso 1 1 calc R . . . .
C25 C 0.0656(4) -0.2871(3) 0.55627(18) 0.0723(7) Uani 1 1 d . . . . .
H25 H -0.000337 -0.387429 0.575429 0.087 Uiso 1 1 calc R . . . .
C26 C 0.1078(4) -0.0942(3) 0.43978(16) 0.0699(7) Uani 1 1 d . . . . .
H26 H 0.068973 -0.065458 0.380125 0.084 Uiso 1 1 calc R . . . .
C27 C 0.0084(5) -0.2427(3) 0.4690(2) 0.0850(9) Uani 1 1 d . . . . .
H27 H -0.097042 -0.312319 0.429399 0.102 Uiso 1 1 calc R . . . .
H15B H 0.411(3) 0.573(2) 0.0433(14) 0.034(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.8334(18) . ?
N1 C2 1.4228(19) . ?
N1 C6 1.371(2) . ?
N1 C7 1.4747(19) . ?
C2 C5 1.394(2) . ?
C2 C8 1.395(2) . ?
O3 C6 1.220(2) . ?
C4 H4 0.9800 . ?
C4 C7 1.536(2) . ?
C4 C12 1.527(2) . ?
C4 C20 1.545(2) . ?
C5 H5 0.9300 . ?
C5 C14 1.385(2) . ?
C6 C20 1.534(2) . ?
C7 H7 0.9800 . ?
C7 C15 1.533(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(2) . ?
C9 H9 0.9300 . ?
C9 C11 1.378(3) . ?
O10 C18 1.206(2) . ?
C11 H11 0.9300 . ?
C11 C14 1.377(3) . ?
C12 H12 0.9800 . ?
C12 C17 1.518(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C20 1.540(2) . ?
C13 C21 1.516(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.96(2) . ?
C15 C19 1.520(2) . ?
C15 H15B 0.98(2) . ?
C16 C18 1.494(3) . ?
C16 C24 1.398(3) . ?
C16 C26 1.383(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C19 1.519(3) . ?
C18 C21 1.517(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C22 1.542(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.380(4) . ?
C23 C25 1.376(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C27 1.373(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(4) . ?
C27 H27 0.9300 . ?

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 N1 C7 120.78(12) . . ?
C6 N1 C2 126.97(13) . . ?
C6 N1 C7 112.07(12) . . ?
C5 C2 N1 122.57(14) . . ?
C5 C2 C8 118.39(14) . . ?
C8 C2 N1 119.04(14) . . ?
C7 C4 H4 106.0 . . ?
C7 C4 C20 105.21(12) . . ?
C12 C4 H4 106.0 . . ?
C12 C4 C7 113.88(12) . . ?
C12 C4 C20 118.76(13) . . ?
C20 C4 H4 106.0 . . ?
C2 C5 H5 120.1 . . ?
C14 C5 C2 119.83(15) . . ?
C14 C5 H5 120.1 . . ?
N1 C6 C20 109.83(13) . . ?
O3 C6 N1 126.03(15) . . ?
O3 C6 C20 124.14(14) . . ?
N1 C7 C4 102.19(11) . . ?
N1 C7 H7 109.0 . . ?
N1 C7 C15 112.10(13) . . ?
C4 C7 H7 109.0 . . ?
C15 C7 C4 115.14(12) . . ?
C15 C7 H7 109.0 . . ?
C2 C8 H8 119.6 . . ?
C9 C8 C2 120.78(16) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C9 C8 120.75(16) . . ?
C11 C9 H9 119.6 . . ?
C9 C11 H11 120.6 . . ?
C14 C11 C9 118.75(16) . . ?
C14 C11 H11 120.6 . . ?
Cl1 C12 H12 109.2 . . ?
C4 C12 Cl1 106.68(11) . . ?
C4 C12 H12 109.2 . . ?
C17 C12 Cl1 106.89(12) . . ?
C17 C12 C4 115.49(14) . . ?
C17 C12 H12 109.2 . . ?
H13A C13 H13B 107.3 . . ?
C20 C13 H13A 108.1 . . ?
C20 C13 H13B 108.1 . . ?
C21 C13 H13A 108.1 . . ?
C21 C13 H13B 108.1 . . ?
C21 C13 C20 116.93(13) . . ?
C5 C14 H14 119.3 . . ?
C11 C14 C5 121.49(16) . . ?
C11 C14 H14 119.3 . . ?
C7 C15 H15A 111.3(12) . . ?
C7 C15 H15B 109.6(11) . . ?
H15A C15 H15B 106.8(16) . . ?
C19 C15 C7 110.92(14) . . ?
C19 C15 H15A 108.9(12) . . ?
C19 C15 H15B 109.2(11) . . ?
C24 C16 C18 118.49(19) . . ?
C26 C16 C18 123.27(17) . . ?
C26 C16 C24 118.2(2) . . ?
C12 C17 H17A 109.2 . . ?
C12 C17 H17B 109.2 . . ?
C12 C17 C19 111.91(14) . . ?
H17A C17 H17B 107.9 . . ?
C19 C17 H17A 109.2 . . ?
C19 C17 H17B 109.2 . . ?
O10 C18 C16 120.78(17) . . ?
O10 C18 C21 120.48(19) . . ?
C16 C18 C21 118.74(16) . . ?
C15 C19 H19A 109.4 . . ?
C15 C19 H19B 109.4 . . ?
C17 C19 C15 111.09(14) . . ?
C17 C19 H19A 109.4 . . ?
C17 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C6 C20 C4 101.03(12) . . ?
C6 C20 C13 111.47(13) . . ?
C6 C20 C22 107.69(14) . . ?
C13 C20 C4 113.58(13) . . ?
C13 C20 C22 107.04(14) . . ?
C22 C20 C4 115.86(14) . . ?
C13 C21 C18 112.74(15) . . ?
C13 C21 H21A 109.0 . . ?
C13 C21 H21B 109.0 . . ?
C18 C21 H21A 109.0 . . ?
C18 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23 119.9 . . ?
C25 C23 H23 119.9 . . ?
C25 C23 C24 120.2(2) . . ?
C16 C24 H24 119.7 . . ?
C23 C24 C16 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C23 C25 H25 120.0 . . ?
C27 C25 C23 120.1(2) . . ?
C27 C25 H25 120.0 . . ?
C16 C26 H26 119.5 . . ?
C16 C26 C27 121.0(2) . . ?
C27 C26 H26 119.5 . . ?
C25 C27 C26 120.0(3) . . ?
C25 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C12 C17 C19 -69.99(17) . . . . ?
N1 C2 C5 C14 -179.04(15) . . . . ?
N1 C2 C8 C9 179.06(16) . . . . ?
N1 C6 C20 C4 17.05(17) . . . . ?
N1 C6 C20 C13 138.02(15) . . . . ?
N1 C6 C20 C22 -104.86(16) . . . . ?
N1 C7 C15 C19 -165.87(13) . . . . ?
C2 N1 C6 O3 -1.8(3) . . . . ?
C2 N1 C6 C20 177.26(14) . . . . ?
C2 N1 C7 C4 164.06(13) . . . . ?
C2 N1 C7 C15 -72.11(17) . . . . ?
C2 C5 C14 C11 -0.1(3) . . . . ?
C2 C8 C9 C11 0.0(3) . . . . ?
O3 C6 C20 C4 -163.84(18) . . . . ?
O3 C6 C20 C13 -42.9(2) . . . . ?
O3 C6 C20 C22 74.3(2) . . . . ?
C4 C7 C15 C19 -49.63(18) . . . . ?
C4 C12 C17 C19 48.5(2) . . . . ?
C5 C2 C8 C9 -1.0(3) . . . . ?
C6 N1 C2 C5 -5.0(2) . . . . ?
C6 N1 C2 C8 174.89(16) . . . . ?
C6 N1 C7 C4 -20.36(16) . . . . ?
C6 N1 C7 C15 103.47(16) . . . . ?
C7 N1 C2 C5 169.86(14) . . . . ?
C7 N1 C2 C8 -10.2(2) . . . . ?
C7 N1 C6 O3 -177.07(18) . . . . ?
C7 N1 C6 C20 2.01(19) . . . . ?
C7 C4 C12 Cl1 79.09(14) . . . . ?
C7 C4 C12 C17 -39.5(2) . . . . ?
C7 C4 C20 C6 -28.76(15) . . . . ?
C7 C4 C20 C13 -148.23(13) . . . . ?
C7 C4 C20 C22 87.25(16) . . . . ?
C7 C15 C19 C17 57.92(19) . . . . ?
C8 C2 C5 C14 1.1(2) . . . . ?
C8 C9 C11 C14 0.9(3) . . . . ?
C9 C11 C14 C5 -0.9(3) . . . . ?
O10 C18 C21 C13 4.7(3) . . . . ?
C12 C4 C7 N1 161.98(13) . . . . ?
C12 C4 C7 C15 40.21(18) . . . . ?
C12 C4 C20 C6 -157.65(14) . . . . ?
C12 C4 C20 C13 82.88(18) . . . . ?
C12 C4 C20 C22 -41.6(2) . . . . ?
C12 C17 C19 C15 -57.6(2) . . . . ?
C16 C18 C21 C13 -175.10(17) . . . . ?
C16 C26 C27 C25 -0.9(5) . . . . ?
C18 C16 C24 C23 179.54(19) . . . . ?
C18 C16 C26 C27 -179.1(3) . . . . ?
C20 C4 C7 N1 30.24(14) . . . . ?
C20 C4 C7 C15 -91.53(15) . . . . ?
C20 C4 C12 Cl1 -156.14(12) . . . . ?
C20 C4 C12 C17 85.26(18) . . . . ?
C20 C13 C21 C18 176.97(15) . . . . ?
C21 C13 C20 C4 62.1(2) . . . . ?
C21 C13 C20 C6 -51.3(2) . . . . ?
C21 C13 C20 C22 -168.79(16) . . . . ?
C23 C25 C27 C26 0.9(5) . . . . ?
C24 C16 C18 O10 -10.9(3) . . . . ?
C24 C16 C18 C21 168.88(18) . . . . ?
C24 C16 C26 C27 0.4(4) . . . . ?
C24 C23 C25 C27 -0.5(4) . . . . ?
C25 C23 C24 C16 0.0(3) . . . . ?
C26 C16 C18 O10 168.5(2) . . . . ?
C26 C16 C18 C21 -11.7(3) . . . . ?
C26 C16 C24 C23 0.1(3) . . . . ?

_olex2_date_sample_data_collection 2019-06-03
_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 3.642
_oxdiff_exptl_absorpt_empirical_full_min 0.640
