# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a
_database_code_depnum_ccdc_archive 'CCDC 1974111'
loop_
_audit_author_name
_audit_author_address
'Hongkai Wang'
;Nankai University
China
;
_audit_update_record             
;
2019-12-26 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N O3'
_chemical_formula_sum            'C27 H22 N O3'
_chemical_formula_weight         408.45
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.242(3)
_cell_length_b                   11.4667(17)
_cell_length_c                   22.485(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4187.6(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    961
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      20.0130
_cell_measurement_theta_min      3.0940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1095
_diffrn_reflns_av_unetI/netI     0.2399
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9885
_diffrn_reflns_point_group_measured_fraction_full 0.808
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         3.094
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -11.00   1.00   10.00    --   18.31   0.00-180.00   42
  2  ω     -7.00  72.00   1.00   10.00    --   18.31   0.00-180.00   79
  3  ω     61.00  87.00   1.00   10.00    --   18.31 178.00 -60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0284653000
_diffrn_orient_matrix_UB_12      -0.0170734000
_diffrn_orient_matrix_UB_13      0.0223031000
_diffrn_orient_matrix_UB_21      -0.0165523000
_diffrn_orient_matrix_UB_22      -0.0425593000
_diffrn_orient_matrix_UB_23      -0.0194929000
_diffrn_orient_matrix_UB_31      0.0286931000
_diffrn_orient_matrix_UB_32      -0.0414817000
_diffrn_orient_matrix_UB_33      0.0108707000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.589
_reflns_Friedel_fraction_full    0.616
_reflns_Friedel_fraction_max     0.616
_reflns_number_gt                2461
_reflns_number_total             5974
_reflns_odcompleteness_completeness 85.45
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         5974
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2131
_refine_ls_R_factor_gt           0.0887
_refine_ls_restrained_S_all      0.931
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1846
_refine_ls_wR_factor_ref         0.2807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Riding coordinates:
 C8(H8A)
2.b Ternary CH refined with riding coordinates:
 C12(H12), C39(H39)
2.c Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C34(H34A,H34B), C23(H23A,H23B), C7(H7A,H7B), C48(H48A,H48B),
 C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C27(H27), C26(H26), C3(H3), C18(H18), C24(H24), C52(H52), C32(H32),
 C30(H30), C4(H4), C25(H25), C50(H50), C33(H33), C5(H5), C53(H53), C28(H28),
 C2(H2), C41(H41), C15(H15), C14(H14), C45(H45), C29(H29), C17(H17), C42(H42),
 C1(H1), C51(H51), C44(H44), C43(H43)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O 0.5820(5) 0.2898(8) 0.5171(4) 0.032(3) Uani 1 1 d . . . . .
O5 O 0.5086(5) 0.7624(7) 0.4670(5) 0.030(2) Uani 1 1 d . . . . .
O2 O 0.7181(5) 0.2346(7) 0.5354(5) 0.033(2) Uani 1 1 d . . . . .
O1 O 0.8426(6) 0.2411(8) 0.4393(5) 0.038(3) Uani 1 1 d . . . . .
O4 O 0.3851(5) 0.7536(7) 0.5628(5) 0.036(3) Uani 1 1 d . . . . .
O6 O 0.6449(5) 0.7094(7) 0.4865(4) 0.030(2) Uani 1 1 d . . . . .
N1 N 0.8384(7) 0.4408(9) 0.4573(5) 0.026(3) Uani 1 1 d . . . . .
N2 N 0.3879(7) 0.5570(9) 0.5466(6) 0.033(3) Uani 1 1 d . . . . .
C8 C 0.7922(8) 0.5221(12) 0.4932(7) 0.028(3) Uani 1 1 d . . . . .
H8A H 0.7683 0.5783 0.4746 0.033 Uiso 1 1 d R . . . .
C11 C 0.8171(8) 0.3282(12) 0.4666(6) 0.028(3) Uani 1 1 d . . . . .
C37 C 0.4877(8) 0.5529(10) 0.4733(6) 0.025(3) Uani 1 1 d . . . . .
C36 C 0.4723(8) 0.6637(11) 0.4894(7) 0.029(4) Uani 1 1 d . . . . .
C12 C 0.6767(8) 0.4786(10) 0.5754(6) 0.024(3) Uani 1 1 d . . . . .
H12 H 0.6299 0.5161 0.5556 0.029 Uiso 1 1 calc R . . . .
C46 C 0.5816(8) 0.6328(11) 0.3974(6) 0.030(4) Uani 1 1 d . . . . .
H46A H 0.5440 0.6528 0.3654 0.036 Uiso 1 1 calc R . . . .
H46B H 0.6352 0.6182 0.3798 0.036 Uiso 1 1 calc R . . . .
C34 C 0.3356(8) 0.5162(12) 0.5944(6) 0.028(3) Uani 1 1 d . . . . .
H34A H 0.2916 0.4691 0.5778 0.033 Uiso 1 1 calc R . . . .
H34B H 0.3108 0.5828 0.6140 0.033 Uiso 1 1 calc R . . . .
C54 C 0.6792(8) 0.8947(12) 0.4521(6) 0.025(3) Uani 1 1 d . . . . .
C35 C 0.4113(8) 0.6683(11) 0.5372(6) 0.025(3) Uani 1 1 d . . . . .
C22 C 0.5487(8) 0.1043(11) 0.5507(6) 0.029(3) Uani 1 1 d . . . . .
C21 C 0.6064(8) 0.1507(11) 0.5892(7) 0.029(4) Uani 1 1 d . . . . .
C38 C 0.4362(9) 0.4748(11) 0.5114(6) 0.026(3) Uani 1 1 d . . . . .
C47 C 0.5884(9) 0.7371(11) 0.4400(7) 0.030(3) Uani 1 1 d . . . . .
C9 C 0.7386(8) 0.4422(11) 0.5294(6) 0.026(3) Uani 1 1 d . . . . .
C10 C 0.7541(7) 0.3338(11) 0.5151(6) 0.024(3) Uani 1 1 d . . . . .
C39 C 0.5513(8) 0.5206(11) 0.4275(6) 0.026(3) Uani 1 1 d . . . . .
H39 H 0.5981 0.4852 0.4482 0.031 Uiso 1 1 calc R . . . .
C13 C 0.7127(9) 0.5617(11) 0.6206(6) 0.034(4) Uani 1 1 d . . . . .
C23 C 0.5412(8) 0.1843(11) 0.4988(6) 0.034(4) Uani 1 1 d . . . . .
H23A H 0.5676 0.1512 0.4640 0.040 Uiso 1 1 calc R . . . .
H23B H 0.4838 0.1993 0.4897 0.040 Uiso 1 1 calc R . . . .
C20 C 0.6384(7) 0.2611(11) 0.5626(7) 0.027(3) Uani 1 1 d . . . . .
C7 C 0.8946(8) 0.4797(12) 0.4095(6) 0.029(3) Uani 1 1 d . . . . .
H7A H 0.9375 0.5285 0.4262 0.035 Uiso 1 1 calc R . . . .
H7B H 0.9205 0.4125 0.3911 0.035 Uiso 1 1 calc R . . . .
C31 C 0.3825(8) 0.4445(12) 0.6398(7) 0.034(4) Uani 1 1 d . . . . .
C6 C 0.8485(8) 0.5456(12) 0.3644(7) 0.030(3) Uani 1 1 d . . . . .
C49 C 0.6214(9) 0.8452(13) 0.4125(7) 0.034(4) Uani 1 1 d . . . . .
C16 C 0.7769(11) 0.7137(15) 0.7055(7) 0.048(4) Uani 1 1 d . . . . .
H16 H 0.7989 0.7643 0.7336 0.058 Uiso 1 1 calc R . . . .
C27 C 0.6228(8) 0.1011(12) 0.6445(8) 0.040(4) Uani 1 1 d . . . . .
H27 H 0.6607 0.1346 0.6703 0.047 Uiso 1 1 calc R . . . .
C26 C 0.5800(9) -0.0015(12) 0.6602(7) 0.042(4) Uani 1 1 d . . . . .
H26 H 0.5879 -0.0364 0.6971 0.051 Uiso 1 1 calc R . . . .
C3 C 0.8487(9) 0.6643(14) 0.3616(8) 0.045(4) Uani 1 1 d . . . . .
H3 H 0.8819 0.7044 0.3884 0.054 Uiso 1 1 calc R . . . .
C18 C 0.7877(8) 0.5407(12) 0.6475(6) 0.036(4) Uani 1 1 d . . . . .
H18 H 0.8169 0.4738 0.6374 0.043 Uiso 1 1 calc R . . . .
C24 C 0.5102(9) 0.0024(13) 0.5652(8) 0.040(4) Uani 1 1 d . . . . .
H24 H 0.4735 -0.0316 0.5387 0.048 Uiso 1 1 calc R . . . .
C52 C 0.7035(10) 1.0474(12) 0.3834(8) 0.045(4) Uani 1 1 d . . . . .
H52 H 0.7310 1.1153 0.3725 0.054 Uiso 1 1 calc R . . . .
C40 C 0.5211(9) 0.4360(11) 0.3825(6) 0.032(4) Uani 1 1 d . . . . .
C32 C 0.3810(9) 0.3205(12) 0.6361(7) 0.035(4) Uani 1 1 d . . . . .
H32 H 0.3482 0.2835 0.6079 0.042 Uiso 1 1 calc R . . . .
C30 C 0.4310(10) 0.4953(14) 0.6812(7) 0.046(4) Uani 1 1 d . . . . .
H30 H 0.4336 0.5762 0.6834 0.055 Uiso 1 1 calc R . . . .
C4 C 0.7524(9) 0.5487(17) 0.2810(8) 0.056(5) Uani 1 1 d . . . . .
H4 H 0.7198 0.5091 0.2537 0.067 Uiso 1 1 calc R . . . .
C25 C 0.5254(9) -0.0495(13) 0.6187(8) 0.045(4) Uani 1 1 d . . . . .
H25 H 0.4987 -0.1190 0.6279 0.054 Uiso 1 1 calc R . . . .
C50 C 0.6052(10) 0.8974(13) 0.3591(6) 0.041(4) Uani 1 1 d . . . . .
H50 H 0.5675 0.8659 0.3324 0.050 Uiso 1 1 calc R . . . .
C33 C 0.4280(9) 0.2570(14) 0.6741(7) 0.043(4) Uani 1 1 d . . . . .
H33 H 0.4282 0.1762 0.6703 0.051 Uiso 1 1 calc R . . . .
C5 C 0.7991(9) 0.4872(13) 0.3215(6) 0.041(4) Uani 1 1 d . . . . .
H5 H 0.7984 0.4061 0.3207 0.049 Uiso 1 1 calc R . . . .
C53 C 0.7196(9) 0.9956(13) 0.4367(8) 0.046(4) Uani 1 1 d . . . . .
H53 H 0.7578 1.0284 0.4626 0.055 Uiso 1 1 calc R . . . .
C28 C 0.4758(10) 0.3072(15) 0.7184(8) 0.052(5) Uani 1 1 d . . . . .
H28 H 0.5054 0.2619 0.7452 0.062 Uiso 1 1 calc R . . . .
C2 C 0.8029(11) 0.7298(15) 0.3213(9) 0.055(5) Uani 1 1 d . . . . .
H2 H 0.8051 0.8109 0.3217 0.066 Uiso 1 1 calc R . . . .
C48 C 0.6865(9) 0.8148(13) 0.5051(8) 0.041(4) Uani 1 1 d . . . . .
H48A H 0.7437 0.7994 0.5145 0.049 Uiso 1 1 calc R . . . .
H48B H 0.6599 0.8485 0.5397 0.049 Uiso 1 1 calc R . . . .
C41 C 0.4416(9) 0.4387(13) 0.3594(8) 0.044(4) Uani 1 1 d . . . . .
H41 H 0.4046 0.4928 0.3748 0.053 Uiso 1 1 calc R . . . .
C15 C 0.7042(12) 0.7360(12) 0.6819(8) 0.050(5) Uani 1 1 d . . . . .
H15 H 0.6758 0.8030 0.6930 0.060 Uiso 1 1 calc R . . . .
C14 C 0.6688(10) 0.6580(13) 0.6394(7) 0.045(4) Uani 1 1 d . . . . .
H14 H 0.6163 0.6721 0.6245 0.055 Uiso 1 1 calc R . . . .
C19 C 0.6474(9) 0.3637(11) 0.6045(7) 0.033(4) Uani 1 1 d . . . . .
H19A H 0.6863 0.3426 0.6355 0.039 Uiso 1 1 calc R . . . .
H19B H 0.5947 0.3777 0.6235 0.039 Uiso 1 1 calc R . . . .
C45 C 0.5719(12) 0.3475(14) 0.3615(8) 0.060(5) Uani 1 1 d . . . . .
H45 H 0.6235 0.3376 0.3787 0.071 Uiso 1 1 calc R . . . .
C29 C 0.4773(10) 0.4282(15) 0.7209(7) 0.050(5) Uani 1 1 d . . . . .
H29 H 0.5097 0.4651 0.7493 0.060 Uiso 1 1 calc R . . . .
C17 C 0.8206(10) 0.6162(14) 0.6889(6) 0.044(4) Uani 1 1 d . . . . .
H17 H 0.8720 0.6013 0.7054 0.053 Uiso 1 1 calc R . . . .
C42 C 0.4146(12) 0.3647(17) 0.3144(8) 0.065(6) Uani 1 1 d . . . . .
H42 H 0.3619 0.3724 0.2986 0.079 Uiso 1 1 calc R . . . .
C1 C 0.7541(10) 0.6714(17) 0.2811(8) 0.058(5) Uani 1 1 d . . . . .
H1 H 0.7223 0.7130 0.2540 0.069 Uiso 1 1 calc R . . . .
C51 C 0.6475(11) 0.9995(14) 0.3466(7) 0.052(5) Uani 1 1 d . . . . .
H51 H 0.6365 1.0370 0.3108 0.063 Uiso 1 1 calc R . . . .
C44 C 0.5487(16) 0.2739(17) 0.3159(11) 0.082(7) Uani 1 1 d . . . . .
H44 H 0.5861 0.2210 0.3000 0.098 Uiso 1 1 calc R . . . .
C43 C 0.4673(18) 0.2798(16) 0.2936(11) 0.088(8) Uani 1 1 d . . . . .
H43 H 0.4495 0.2267 0.2651 0.106 Uiso 1 1 calc R . . . .
H38A H 0.404(9) 0.426(12) 0.484(7) 0.05(5) Uiso 1 1 d . . . . .
H38B H 0.483(6) 0.431(8) 0.541(5) 0.02(3) Uiso 1 1 d . . . . .
H8B H 0.835(8) 0.565(11) 0.522(6) 0.05(4) 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
O3 C23 1.439(14) . ?
O3 C20 1.411(17) . ?
O5 C36 1.372(15) . ?
O5 C47 1.461(16) . ?
O2 C10 1.358(14) . ?
O2 C20 1.463(15) . ?
O1 C11 1.244(15) . ?
O4 C35 1.211(14) . ?
O6 C47 1.428(16) . ?
O6 C48 1.446(16) . ?
N1 C8 1.445(17) . ?
N1 C11 1.352(16) . ?
N1 C7 1.478(16) . ?
N2 C34 1.447(17) . ?
N2 C35 1.349(16) . ?
N2 C38 1.460(17) . ?
C8 H8A 0.8600 . ?
C8 C9 1.504(18) . ?
C8 H8B 1.07(14) . ?
C11 C10 1.496(18) . ?
C37 C36 1.345(17) . ?
C37 C38 1.494(18) . ?
C37 C39 1.506(18) . ?
C36 C35 1.463(18) . ?
C12 H12 0.9800 . ?
C12 C9 1.502(18) . ?
C12 C13 1.511(18) . ?
C12 C19 1.546(17) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 C47 1.537(18) . ?
C46 C39 1.534(17) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C31 1.517(19) . ?
C54 C49 1.412(19) . ?
C54 C53 1.374(19) . ?
C54 C48 1.51(2) . ?
C22 C21 1.383(19) . ?
C22 C23 1.489(18) . ?
C22 C24 1.364(19) . ?
C21 C20 1.494(18) . ?
C21 C27 1.39(2) . ?
C38 H38A 0.98(15) . ?
C38 H38B 1.13(11) . ?
C47 C49 1.48(2) . ?
C9 C10 1.308(17) . ?
C39 H39 0.9800 . ?
C39 C40 1.485(19) . ?
C13 C18 1.382(18) . ?
C13 C14 1.381(18) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C20 C19 1.515(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.468(19) . ?
C31 C32 1.425(18) . ?
C31 C30 1.35(2) . ?
C6 C3 1.36(2) . ?
C6 C5 1.423(19) . ?
C49 C50 1.37(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.32(2) . ?
C16 C17 1.38(2) . ?
C27 H27 0.9300 . ?
C27 C26 1.412(18) . ?
C26 H26 0.9300 . ?
C26 C25 1.40(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.39(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.378(19) . ?
C24 H24 0.9300 . ?
C24 C25 1.36(2) . ?
C52 H52 0.9300 . ?
C52 C53 1.36(2) . ?
C52 C51 1.35(2) . ?
C40 C41 1.393(19) . ?
C40 C45 1.390(19) . ?
C32 H32 0.9300 . ?
C32 C33 1.36(2) . ?
C30 H30 0.9300 . ?
C30 C29 1.40(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.38(2) . ?
C4 C1 1.41(2) . ?
C25 H25 0.9300 . ?
C50 H50 0.9300 . ?
C50 C51 1.39(2) . ?
C33 H33 0.9300 . ?
C33 C28 1.39(2) . ?
C5 H5 0.9300 . ?
C53 H53 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.39(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.38(2) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C41 H41 0.9300 . ?
C41 C42 1.39(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.43(2) . ?
C14 H14 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C45 H45 0.9300 . ?
C45 C44 1.38(3) . ?
C29 H29 0.9300 . ?
C17 H17 0.9300 . ?
C42 H42 0.9300 . ?
C42 C43 1.38(3) . ?
C1 H1 0.9300 . ?
C51 H51 0.9300 . ?
C44 H44 0.9300 . ?
C44 C43 1.42(3) . ?
C43 H43 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
C20 O3 C23 108.1(10) . . ?
C36 O5 C47 111.7(9) . . ?
C10 O2 C20 110.3(9) . . ?
C47 O6 C48 109.0(10) . . ?
C8 N1 C7 122.2(10) . . ?
C11 N1 C8 113.3(11) . . ?
C11 N1 C7 124.0(12) . . ?
C34 N2 C38 120.6(11) . . ?
C35 N2 C34 126.0(12) . . ?
C35 N2 C38 112.0(11) . . ?
N1 C8 H8A 116.4 . . ?
N1 C8 C9 102.1(10) . . ?
N1 C8 H8B 108(7) . . ?
H8A C8 H8B 104.0 . . ?
C9 C8 H8A 117.3 . . ?
C9 C8 H8B 109(7) . . ?
O1 C11 N1 127.1(13) . . ?
O1 C11 C10 128.5(12) . . ?
N1 C11 C10 104.3(12) . . ?
C36 C37 C38 108.0(12) . . ?
C36 C37 C39 122.9(12) . . ?
C38 C37 C39 128.9(10) . . ?
O5 C36 C35 122.1(12) . . ?
C37 C36 O5 126.9(13) . . ?
C37 C36 C35 110.9(13) . . ?
C9 C12 H12 109.1 . . ?
C9 C12 C13 112.4(11) . . ?
C9 C12 C19 105.1(10) . . ?
C13 C12 H12 109.1 . . ?
C13 C12 C19 111.8(12) . . ?
C19 C12 H12 109.1 . . ?
H46A C46 H46B 107.7 . . ?
C47 C46 H46A 108.8 . . ?
C47 C46 H46B 108.8 . . ?
C39 C46 H46A 108.8 . . ?
C39 C46 H46B 108.8 . . ?
C39 C46 C47 113.6(11) . . ?
N2 C34 H34A 109.1 . . ?
N2 C34 H34B 109.1 . . ?
N2 C34 C31 112.4(11) . . ?
H34A C34 H34B 107.9 . . ?
C31 C34 H34A 109.1 . . ?
C31 C34 H34B 109.1 . . ?
C49 C54 C48 107.8(12) . . ?
C53 C54 C49 119.8(14) . . ?
C53 C54 C48 132.3(14) . . ?
O4 C35 N2 126.2(13) . . ?
O4 C35 C36 128.0(12) . . ?
N2 C35 C36 105.8(12) . . ?
C21 C22 C23 108.0(11) . . ?
C24 C22 C21 119.3(14) . . ?
C24 C22 C23 132.7(14) . . ?
C22 C21 C20 108.1(12) . . ?
C22 C21 C27 122.1(13) . . ?
C27 C21 C20 129.6(13) . . ?
N2 C38 C37 103.0(10) . . ?
N2 C38 H38A 115(9) . . ?
N2 C38 H38B 109(5) . . ?
C37 C38 H38A 107(9) . . ?
C37 C38 H38B 103(5) . . ?
H38A C38 H38B 118(10) . . ?
O5 C47 C46 110.5(11) . . ?
O5 C47 C49 109.1(10) . . ?
O6 C47 O5 108.1(11) . . ?
O6 C47 C46 109.3(11) . . ?
O6 C47 C49 105.0(12) . . ?
C49 C47 C46 114.6(12) . . ?
C12 C9 C8 126.2(11) . . ?
C10 C9 C8 109.5(12) . . ?
C10 C9 C12 124.3(12) . . ?
O2 C10 C11 120.3(11) . . ?
C9 C10 O2 129.0(12) . . ?
C9 C10 C11 110.6(12) . . ?
C37 C39 C46 108.4(10) . . ?
C37 C39 H39 108.0 . . ?
C46 C39 H39 108.0 . . ?
C40 C39 C37 113.6(11) . . ?
C40 C39 C46 110.7(11) . . ?
C40 C39 H39 108.0 . . ?
C18 C13 C12 121.7(12) . . ?
C14 C13 C12 120.7(14) . . ?
C14 C13 C18 117.4(14) . . ?
O3 C23 C22 104.9(11) . . ?
O3 C23 H23A 110.8 . . ?
O3 C23 H23B 110.8 . . ?
C22 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
H23A C23 H23B 108.8 . . ?
O3 C20 O2 108.7(12) . . ?
O3 C20 C21 105.2(10) . . ?
O3 C20 C19 109.5(11) . . ?
O2 C20 C21 107.4(10) . . ?
O2 C20 C19 109.6(10) . . ?
C21 C20 C19 116.2(13) . . ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C6 C7 N1 110.0(11) . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C32 C31 C34 119.5(13) . . ?
C30 C31 C34 121.6(13) . . ?
C30 C31 C32 118.8(15) . . ?
C3 C6 C7 123.1(14) . . ?
C3 C6 C5 116.1(15) . . ?
C5 C6 C7 120.9(13) . . ?
C54 C49 C47 108.3(14) . . ?
C50 C49 C54 120.3(14) . . ?
C50 C49 C47 131.4(15) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.7(16) . . ?
C17 C16 H16 119.7 . . ?
C21 C27 H27 121.0 . . ?
C21 C27 C26 118.0(14) . . ?
C26 C27 H27 121.0 . . ?
C27 C26 H26 120.9 . . ?
C25 C26 C27 118.2(15) . . ?
C25 C26 H26 120.9 . . ?
C6 C3 H3 117.7 . . ?
C6 C3 C2 124.7(16) . . ?
C2 C3 H3 117.7 . . ?
C13 C18 H18 119.1 . . ?
C17 C18 C13 121.8(14) . . ?
C17 C18 H18 119.1 . . ?
C22 C24 H24 119.9 . . ?
C22 C24 C25 120.1(15) . . ?
C25 C24 H24 119.9 . . ?
C53 C52 H52 120.3 . . ?
C51 C52 H52 120.3 . . ?
C51 C52 C53 119.4(15) . . ?
C41 C40 C39 123.1(13) . . ?
C45 C40 C39 120.8(14) . . ?
C45 C40 C41 116.1(15) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 C31 119.2(15) . . ?
C33 C32 H32 120.4 . . ?
C31 C30 H30 119.5 . . ?
C31 C30 C29 121.1(15) . . ?
C29 C30 H30 119.5 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C1 120.0(16) . . ?
C1 C4 H4 120.0 . . ?
C26 C25 H25 119.0 . . ?
C24 C25 C26 122.0(14) . . ?
C24 C25 H25 119.0 . . ?
C49 C50 H50 121.6 . . ?
C49 C50 C51 116.9(15) . . ?
C51 C50 H50 121.6 . . ?
C32 C33 H33 118.5 . . ?
C32 C33 C28 123.0(16) . . ?
C28 C33 H33 118.5 . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.2(15) . . ?
C4 C5 H5 119.4 . . ?
C54 C53 H53 120.1 . . ?
C52 C53 C54 119.8(16) . . ?
C52 C53 H53 120.1 . . ?
C33 C28 H28 121.5 . . ?
C33 C28 C29 117.0(15) . . ?
C29 C28 H28 121.5 . . ?
C3 C2 H2 120.9 . . ?
C1 C2 C3 118.2(16) . . ?
C1 C2 H2 120.9 . . ?
O6 C48 C54 104.0(12) . . ?
O6 C48 H48A 111.0 . . ?
O6 C48 H48B 111.0 . . ?
C54 C48 H48A 111.0 . . ?
C54 C48 H48B 111.0 . . ?
H48A C48 H48B 109.0 . . ?
C40 C41 H41 118.3 . . ?
C42 C41 C40 123.3(16) . . ?
C42 C41 H41 118.3 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.5(15) . . ?
C14 C15 H15 119.8 . . ?
C13 C14 C15 119.8(15) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C12 C19 H19A 108.5 . . ?
C12 C19 H19B 108.5 . . ?
C20 C19 C12 115.3(12) . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C40 C45 H45 118.8 . . ?
C44 C45 C40 122(2) . . ?
C44 C45 H45 118.8 . . ?
C30 C29 H29 119.5 . . ?
C28 C29 C30 121.0(15) . . ?
C28 C29 H29 119.5 . . ?
C16 C17 C18 119.6(16) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C41 C42 H42 120.6 . . ?
C43 C42 C41 119(2) . . ?
C43 C42 H42 120.6 . . ?
C4 C1 H1 120.0 . . ?
C2 C1 C4 119.9(17) . . ?
C2 C1 H1 120.0 . . ?
C52 C51 C50 123.8(15) . . ?
C52 C51 H51 118.1 . . ?
C50 C51 H51 118.1 . . ?
C45 C44 H44 120.4 . . ?
C45 C44 C43 119(2) . . ?
C43 C44 H44 120.4 . . ?
C42 C43 C44 120(2) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?

_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1974116'
loop_
_audit_author_name
_audit_author_address
'Hongkai Wang'
;Nankai University
China
;
_audit_update_record             
;
2019-12-26 deposited with the CCDC.	2020-05-21 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)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H22 Br N O3, C H2 Cl2'
_chemical_formula_sum            'C28 H24 Br Cl2 N O3'
_chemical_formula_weight         573.29
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.1230(9)
_cell_length_b                   11.6920(12)
_cell_length_c                   12.5199(16)
_cell_angle_alpha                112.093(11)
_cell_angle_beta                 106.874(10)
_cell_angle_gamma                97.913(8)
_cell_volume                     1262.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1708
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      24.4430
_cell_measurement_theta_min      3.2540
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             584
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7421
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.11
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_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     -9.00  32.00   1.00    3.00    --   18.78  77.00   0.00   41
  2  ω     36.00  61.00   1.00    3.00    --   18.78 -99.00 120.00   25
  3  ω    -10.00  89.00   1.00    3.00    --   18.78  77.00-120.00   99
  4  ω    -46.00  50.00   1.00    3.00    --  -20.03  37.00 150.00   96
  5  ω    -90.00   5.00   1.00    3.00    --  -20.03 -37.00 -30.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0691603000
_diffrn_orient_matrix_UB_12      0.0447598000
_diffrn_orient_matrix_UB_13      0.0321289000
_diffrn_orient_matrix_UB_21      0.0004751000
_diffrn_orient_matrix_UB_22      -0.0012419000
_diffrn_orient_matrix_UB_23      0.0563159000
_diffrn_orient_matrix_UB_31      0.0320681000
_diffrn_orient_matrix_UB_32      -0.0513994000
_diffrn_orient_matrix_UB_33      -0.0117437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3303
_reflns_number_total             4434
_reflns_odcompleteness_completeness 85.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0247P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0860
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
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), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C27(H27), C24(H24), C19(H19), C26(H26), C20(H20), C21(H21), C4(H4),
 C18(H18), C7(H7), C22(H22), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 1.15997(4) 0.38786(4) 0.77174(4) 0.03119(13) Uani 1 d . . .
Cl2 Cl 0.46102(11) 0.28116(11) -0.06124(9) 0.0433(3) Uani 1 d . . .
Cl1 Cl 0.30121(11) 0.29401(10) 0.09948(9) 0.0492(3) Uani 1 d . . .
O3 O 0.8969(2) 0.3013(2) 0.3722(2) 0.0229(6) Uani 1 d . . .
O1 O 0.5869(2) 0.5846(2) 0.3304(2) 0.0280(6) Uani 1 d . . .
O2 O 0.7015(2) 0.3736(2) 0.2944(2) 0.0229(6) Uani 1 d . . .
N14 N 0.6855(3) 0.6378(3) 0.5392(3) 0.0230(7) Uani 1 d . . .
C11 C 0.7865(3) 0.4672(3) 0.5256(3) 0.0182(8) Uani 1 d . . .
C23 C 0.8610(4) 0.3761(3) 0.6817(3) 0.0203(8) Uani 1 d . . .
C10 C 0.8836(3) 0.3977(3) 0.5747(3) 0.0204(8) Uani 1 d . . .
H10 H 0.9816 0.4538 0.6088 0.025 Uiso 1 calc . . R
C12 C 0.7181(3) 0.4548(3) 0.4113(3) 0.0193(8) Uani 1 d . . .
C3 C 0.6696(4) 0.1634(3) 0.2930(3) 0.0232(9) Uani 1 d . . .
C8 C 0.7385(4) 0.1692(3) 0.4079(3) 0.0214(8) Uani 1 d . . .
C15 C 0.7719(4) 0.5892(3) 0.6166(3) 0.0252(9) Uani 1 d . . .
H15A H 0.7246 0.5711 0.6680 0.030 Uiso 1 calc . . R
H15B H 0.8653 0.6505 0.6699 0.030 Uiso 1 calc . . R
C13 C 0.6532(4) 0.5640(3) 0.4164(3) 0.0221(8) Uani 1 d . . .
C25 C 0.7004(4) 0.3365(3) 0.7829(3) 0.0263(9) Uani 1 d . . .
H25 H 0.6086 0.3250 0.7849 0.032 Uiso 1 calc . . R
C9 C 0.8795(4) 0.2726(3) 0.4709(3) 0.0239(8) Uani 1 d . . .
H9 H 0.9577 0.2390 0.5028 0.029 Uiso 1 calc . . R
C27 C 0.9493(4) 0.3498(3) 0.8711(3) 0.0260(9) Uani 1 d . . .
H27 H 1.0253 0.3469 0.9324 0.031 Uiso 1 calc . . R
C24 C 0.7246(4) 0.3567(3) 0.6875(3) 0.0221(8) Uani 1 d . . .
H24 H 0.6478 0.3573 0.6253 0.026 Uiso 1 calc . . R
C16 C 0.7939(4) 0.8711(3) 0.6590(3) 0.0219(8) Uani 1 d . . .
C28 C 0.9712(4) 0.3703(3) 0.7750(3) 0.0240(8) Uani 1 d . . .
C19 C 0.9971(4) 1.0009(3) 0.6560(4) 0.0337(10) Uani 1 d . . .
H19 H 1.0461 1.0233 0.6112 0.040 Uiso 1 calc . . R
C26 C 0.8126(4) 0.3334(3) 0.8754(3) 0.0283(9) Uani 1 d . . .
H26 H 0.7967 0.3205 0.9400 0.034 Uiso 1 calc . . R
C2 C 0.7609(4) 0.2638(3) 0.2773(3) 0.0232(8) Uani 1 d . . .
C20 C 1.0547(4) 1.0618(3) 0.7835(4) 0.0336(10) Uani 1 d . . .
H20 H 1.1420 1.1252 0.8252 0.040 Uiso 1 calc . . R
C21 C 0.9813(4) 1.0276(4) 0.8491(4) 0.0353(10) Uani 1 d . . .
H21 H 1.0190 1.0686 0.9355 0.042 Uiso 1 calc . . R
C4 C 0.5387(4) 0.0738(3) 0.2116(3) 0.0304(9) Uani 1 d . . .
H4 H 0.4930 0.0706 0.1341 0.036 Uiso 1 calc . . R
C18 C 0.8673(4) 0.9069(3) 0.5937(3) 0.0307(9) Uani 1 d . . .
H18 H 0.8288 0.8674 0.5073 0.037 Uiso 1 calc . . R
C17 C 0.6564(4) 0.7621(3) 0.5895(3) 0.0271(9) Uani 1 d . . .
H17A H 0.6067 0.7629 0.6453 0.032 Uiso 1 calc . . R
H17B H 0.5940 0.7747 0.5221 0.032 Uiso 1 calc . . R
C7 C 0.6789(4) 0.0847(3) 0.4463(4) 0.0291(9) Uani 1 d . . .
H7 H 0.7250 0.0884 0.5240 0.035 Uiso 1 calc . . R
C22 C 0.8527(4) 0.9331(3) 0.7875(3) 0.0315(9) Uani 1 d . . .
H22 H 0.8045 0.9106 0.8327 0.038 Uiso 1 calc . . R
C5 C 0.4778(4) -0.0109(3) 0.2488(4) 0.0341(10) Uani 1 d . . .
H5 H 0.3898 -0.0714 0.1959 0.041 Uiso 1 calc . . R
C29 C 0.4191(4) 0.3834(3) 0.0612(3) 0.0316(9) Uani 1 d . . .
H29A H 0.3747 0.4427 0.0370 0.038 Uiso 1 calc . . R
H29B H 0.5068 0.4333 0.1335 0.038 Uiso 1 calc . . R
C6 C 0.5473(4) -0.0059(3) 0.3642(4) 0.0355(10) Uani 1 d . . .
H6 H 0.5055 -0.0640 0.3874 0.043 Uiso 1 calc . . R
C1 C 0.7784(4) 0.2251(4) 0.1535(3) 0.0342(10) Uani 1 d . . .
H1A H 0.8423 0.2958 0.1563 0.051 Uiso 1 calc . . GR
H1B H 0.6864 0.2021 0.0891 0.051 Uiso 1 calc . . GR
H1C H 0.8174 0.1528 0.1367 0.051 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C28 1.908(3) . ?
Cl2 C29 1.760(3) . ?
Cl1 C29 1.764(3) . ?
O3 C9 1.446(4) . ?
O3 C2 1.411(4) . ?
O1 C13 1.219(4) . ?
O2 C12 1.356(4) . ?
O2 C2 1.462(4) . ?
N14 C15 1.445(4) . ?
N14 C13 1.359(4) . ?
N14 C17 1.461(4) . ?
C11 C10 1.499(4) . ?
C11 C12 1.337(4) . ?
C11 C15 1.513(4) . ?
C23 C10 1.526(4) . ?
C23 C24 1.394(4) . ?
C23 C28 1.392(5) . ?
C10 H10 0.9800 . ?
C10 C9 1.534(4) . ?
C12 C13 1.504(4) . ?
C3 C8 1.376(5) . ?
C3 C2 1.500(5) . ?
C3 C4 1.387(5) . ?
C8 C9 1.509(5) . ?
C8 C7 1.390(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C25 H25 0.9300 . ?
C25 C24 1.382(5) . ?
C25 C26 1.382(5) . ?
C9 H9 0.9800 . ?
C27 H27 0.9300 . ?
C27 C28 1.383(5) . ?
C27 C26 1.390(4) . ?
C24 H24 0.9300 . ?
C16 C18 1.387(5) . ?
C16 C17 1.514(4) . ?
C16 C22 1.384(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.374(5) . ?
C19 C18 1.380(5) . ?
C26 H26 0.9300 . ?
C2 C1 1.513(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(5) . ?
C18 H18 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C6 1.397(5) . ?
C22 H22 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.386(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C6 H6 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O3 C9 109.1(2) . . ?
C12 O2 C2 118.4(3) . . ?
C15 N14 C17 122.8(3) . . ?
C13 N14 C15 112.2(3) . . ?
C13 N14 C17 124.4(3) . . ?
C10 C11 C15 118.8(3) . . ?
C12 C11 C10 133.2(3) . . ?
C12 C11 C15 107.4(3) . . ?
C24 C23 C10 120.4(3) . . ?
C28 C23 C10 122.8(3) . . ?
C28 C23 C24 116.7(3) . . ?
C11 C10 C23 114.2(3) . . ?
C11 C10 H10 106.1 . . ?
C11 C10 C9 112.0(3) . . ?
C23 C10 H10 106.1 . . ?
C23 C10 C9 111.7(3) . . ?
C9 C10 H10 106.1 . . ?
O2 C12 C13 113.1(3) . . ?
C11 C12 O2 135.7(3) . . ?
C11 C12 C13 111.0(3) . . ?
C8 C3 C2 108.6(3) . . ?
C8 C3 C4 121.5(3) . . ?
C4 C3 C2 130.0(4) . . ?
C3 C8 C9 108.3(3) . . ?
C3 C8 C7 120.9(3) . . ?
C7 C8 C9 130.8(3) . . ?
N14 C15 C11 104.4(3) . . ?
N14 C15 H15A 110.9 . . ?
N14 C15 H15B 110.9 . . ?
C11 C15 H15A 110.9 . . ?
C11 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
O1 C13 N14 126.5(3) . . ?
O1 C13 C12 128.4(3) . . ?
N14 C13 C12 105.1(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 120.0(3) . . ?
O3 C9 C10 107.9(3) . . ?
O3 C9 C8 103.8(3) . . ?
O3 C9 H9 109.9 . . ?
C10 C9 H9 109.9 . . ?
C8 C9 C10 115.2(3) . . ?
C8 C9 H9 109.9 . . ?
C28 C27 H27 120.3 . . ?
C28 C27 C26 119.4(3) . . ?
C26 C27 H27 120.3 . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.9(3) . . ?
C25 C24 H24 119.1 . . ?
C18 C16 C17 119.8(3) . . ?
C22 C16 C18 118.4(3) . . ?
C22 C16 C17 121.7(3) . . ?
C23 C28 Br1 120.1(3) . . ?
C27 C28 Br1 117.5(3) . . ?
C27 C28 C23 122.4(3) . . ?
C20 C19 H19 119.7 . . ?
C20 C19 C18 120.6(4) . . ?
C18 C19 H19 119.7 . . ?
C25 C26 C27 119.6(3) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
O3 C2 O2 110.0(3) . . ?
O3 C2 C3 104.8(3) . . ?
O3 C2 C1 109.3(3) . . ?
O2 C2 C3 110.0(3) . . ?
O2 C2 C1 105.3(3) . . ?
C3 C2 C1 117.3(3) . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(4) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.3(4) . . ?
C22 C21 H21 119.8 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.9 . . ?
C16 C18 H18 119.8 . . ?
C19 C18 C16 120.5(4) . . ?
C19 C18 H18 119.8 . . ?
N14 C17 C16 111.3(3) . . ?
N14 C17 H17A 109.4 . . ?
N14 C17 H17B 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C8 C7 H7 121.1 . . ?
C8 C7 C6 117.7(4) . . ?
C6 C7 H7 121.1 . . ?
C16 C22 H22 119.5 . . ?
C21 C22 C16 120.9(4) . . ?
C21 C22 H22 119.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
Cl2 C29 Cl1 110.83(19) . . ?
Cl2 C29 H29A 109.5 . . ?
Cl2 C29 H29B 109.5 . . ?
Cl1 C29 H29A 109.5 . . ?
Cl1 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C7 C6 H6 119.4 . . ?
C5 C6 C7 121.2(4) . . ?
C5 C6 H6 119.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_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 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.674
