#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:46:55 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/42/7134224.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134224
loop_
_publ_author_name
'Huang, Xuelian'
'Yang, Gaosheng'
'Chai, Zhuo'
_publ_section_title
;
 Diastereoselective synthesis of benzazocines by
 Zn(OTf)₂-catalyzed (4+4) cyclocondensation of multisubstituted
 donor-acceptor cyclopropanes with anthranils.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3704
_journal_page_last               3707
_journal_paper_doi               10.1039/d4cc06690a
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H26 Br N O5'
_chemical_formula_sum            'C34 H26 Br N O5'
_chemical_formula_weight         608.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-04-18 deposited with the CCDC.	2025-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4122(6)
_cell_length_b                   13.8828(10)
_cell_length_c                   19.5704(13)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.512
_cell_measurement_theta_min      2.546
_cell_volume                     2828.9(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            79600
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.547
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0941 before and 0.0758 after correction. The Ratio of minimum to maximum transmission is 0.7849. The λ/2 correction factor is Not present.'
_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    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1338 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0369
_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)+(0.0321P)²+0.9708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3715
_reflns_number_total             4978
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc06690a2.cif
_cod_data_source_block           mo_20240413b_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134221--7134226.cif.'
_cod_database_code               7134224
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.744
_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:
 C00H(H00H), C00I(H00I), C00X(H00X)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00P(H00P),
 C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W), C00Y(H00Y),
 C00Z(H00Z), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015)
2.d Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
Br01 Br 0.51400(7) 0.70382(6) 0.79815(3) 0.0962(3) Uani 1 1 d . . . . .
O002 O 0.3816(2) 0.7985(2) 0.43948(14) 0.0421(7) Uani 1 1 d . . . . .
O003 O 0.5522(3) 0.8156(2) 0.27435(13) 0.0451(7) Uani 1 1 d . . . . .
O004 O 0.7280(4) 0.5556(2) 0.38691(18) 0.0607(10) Uani 1 1 d . . . . .
O005 O 0.6542(3) 0.7193(3) 0.20029(16) 0.0601(9) Uani 1 1 d . . . . .
N006 N 0.3807(3) 0.6957(3) 0.45908(17) 0.0396(8) Uani 1 1 d . . . . .
O007 O 0.7627(5) 0.5504(3) 0.2743(2) 0.0871(14) Uani 1 1 d . . . . .
C008 C 0.6129(3) 0.7379(3) 0.3758(2) 0.0359(10) Uani 1 1 d . . . . .
C009 C 0.3437(4) 0.7085(4) 0.3418(2) 0.0439(11) Uani 1 1 d . . . . .
C00A C 0.5173(4) 0.6741(3) 0.56083(19) 0.0381(9) Uani 1 1 d . . . . .
C00B C 0.6258(4) 0.7361(3) 0.2581(2) 0.0446(11) Uani 1 1 d . . . . .
C00C C 0.5377(4) 0.8234(3) 0.34821(19) 0.0379(10) Uani 1 1 d . . . . .
C00D C 0.7221(4) 0.5902(3) 0.3237(2) 0.0447(11) Uani 1 1 d . . . . .
C00E C 0.6569(4) 0.6860(3) 0.3230(2) 0.0364(10) Uani 1 1 d . . . . .
C00F C 0.7081(4) 0.9331(3) 0.3967(2) 0.0464(11) Uani 1 1 d . . . . .
H00F H 0.762754 0.880230 0.399494 0.056 Uiso 1 1 calc R . . . .
C00G C 0.6226(4) 0.7237(3) 0.4515(2) 0.0347(9) Uani 1 1 d . . . . .
H00A H 0.626166 0.786484 0.473261 0.042 Uiso 1 1 calc R . . . .
H00B H 0.702599 0.690846 0.461485 0.042 Uiso 1 1 calc R . . . .
C00H C 0.5108(4) 0.6657(3) 0.48362(18) 0.0374(9) Uani 1 1 d . . . . .
H00H H 0.522946 0.597738 0.471618 0.045 Uiso 1 1 calc R . . . .
C00I C 0.3934(4) 0.8035(3) 0.3659(2) 0.0416(10) Uani 1 1 d . . . . .
H00I H 0.339431 0.855638 0.348091 0.050 Uiso 1 1 calc R . . . .
C00J C 0.7508(5) 1.0228(3) 0.4177(3) 0.0542(13) Uani 1 1 d . . . . .
H00J H 0.833683 1.029600 0.434769 0.065 Uiso 1 1 calc R . . . .
C00K C 0.4887(4) 0.7700(4) 0.6624(2) 0.0531(12) Uani 1 1 d . . . . .
H00K H 0.469092 0.828511 0.683030 0.064 Uiso 1 1 calc R . . . .
C00L C 0.5071(5) 1.0029(3) 0.3656(2) 0.0501(11) Uani 1 1 d . . . . .
H00L H 0.425134 0.997115 0.347222 0.060 Uiso 1 1 calc R . . . .
C00M C 0.5538(4) 0.5973(3) 0.6018(2) 0.0503(12) Uani 1 1 d . . . . .
H00M H 0.577759 0.539590 0.581330 0.060 Uiso 1 1 calc R . . . .
C00N C 0.5203(4) 0.6907(4) 0.7017(2) 0.0538(12) Uani 1 1 d . . . . .
C00O C 0.5848(4) 0.9212(3) 0.3715(2) 0.0396(10) Uani 1 1 d . . . . .
C00P C 0.5505(5) 1.0924(4) 0.3868(3) 0.0577(13) Uani 1 1 d . . . . .
H00P H 0.497528 1.146065 0.382933 0.069 Uiso 1 1 calc R . . . .
C00Q C 0.3409(4) 0.6480(3) 0.3975(2) 0.0452(11) Uani 1 1 d . . . . .
C00R C 0.5553(4) 0.6045(4) 0.6721(3) 0.0584(14) Uani 1 1 d . . . . .
H00R H 0.579439 0.552273 0.698972 0.070 Uiso 1 1 calc R . . . .
C00S C 0.4867(4) 0.7611(3) 0.5924(2) 0.0464(10) Uani 1 1 d . . . . .
H00S H 0.464466 0.813953 0.565688 0.056 Uiso 1 1 calc R . . . .
C00T C 0.6717(5) 1.1019(4) 0.4136(3) 0.0583(13) Uani 1 1 d . . . . .
H00T H 0.700260 1.161655 0.428889 0.070 Uiso 1 1 calc R . . . .
C00U C 0.6955(5) 0.4049(3) 0.4435(3) 0.0526(12) Uani 1 1 d . . . . .
C00V C 0.5746(6) 0.3785(4) 0.4169(3) 0.0676(15) Uani 1 1 d . . . . .
H00V H 0.553624 0.393452 0.371937 0.081 Uiso 1 1 calc R . . . .
C00W C 0.3081(4) 0.6747(4) 0.2778(2) 0.0583(14) Uani 1 1 d . . . . .
H00W H 0.309712 0.714858 0.239759 0.070 Uiso 1 1 calc R . . . .
C00X C 0.7876(5) 0.4598(3) 0.3978(3) 0.0575(13) Uani 1 1 d . . . . .
H00X H 0.795384 0.426395 0.353901 0.069 Uiso 1 1 calc R . . . .
C00Y C 0.4873(6) 0.3305(4) 0.4577(4) 0.0774(16) Uani 1 1 d . . . . .
H00Y H 0.407506 0.313774 0.439899 0.093 Uiso 1 1 calc R . . . .
C00Z C 0.3031(5) 0.5528(4) 0.3925(3) 0.0572(14) Uani 1 1 d . . . . .
H00Z H 0.301209 0.512640 0.430502 0.069 Uiso 1 1 calc R . . . .
C010 C 0.9198(5) 0.4771(4) 0.4271(3) 0.0729(16) Uani 1 1 d . . . . .
H01A H 0.970531 0.512559 0.394707 0.109 Uiso 1 1 calc GR . . . .
H01B H 0.960416 0.416432 0.436393 0.109 Uiso 1 1 calc GR . . . .
H01C H 0.912621 0.513381 0.468646 0.109 Uiso 1 1 calc GR . . . .
C011 C 0.2701(5) 0.5793(5) 0.2720(3) 0.0665(16) Uani 1 1 d . . . . .
H011 H 0.245672 0.555315 0.229601 0.080 Uiso 1 1 calc R . . . .
C012 C 0.7238(5) 0.3809(4) 0.5097(3) 0.0630(14) Uani 1 1 d . . . . .
H012 H 0.803054 0.397749 0.528093 0.076 Uiso 1 1 calc R . . . .
C013 C 0.2678(6) 0.5196(4) 0.3280(3) 0.0715(17) Uani 1 1 d . . . . .
H013 H 0.242313 0.455877 0.322778 0.086 Uiso 1 1 calc R . . . .
C014 C 0.5164(6) 0.3070(4) 0.5238(3) 0.0790(16) Uani 1 1 d . . . . .
H014 H 0.456593 0.275086 0.550895 0.095 Uiso 1 1 calc R . . . .
C015 C 0.6344(6) 0.3311(4) 0.5498(3) 0.0750(16) Uani 1 1 d . . . . .
H015 H 0.655269 0.314297 0.594456 0.090 Uiso 1 1 calc R . . . .
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'
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'
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
C00I O002 N006 107.8(3) . . ?
C00B O003 C00C 110.2(3) . . ?
C00D O004 C00X 118.6(4) . . ?
O002 N006 C00H 110.3(3) . . ?
C00Q N006 O002 103.2(3) . . ?
C00Q N006 C00H 113.7(3) . . ?
C00E C008 C00C 108.7(4) . . ?
C00E C008 C00G 132.0(4) . . ?
C00G C008 C00C 119.2(4) . . ?
C00Q C009 C00I 107.3(4) . . ?
C00Q C009 C00W 120.2(5) . . ?
C00W C009 C00I 132.5(5) . . ?
C00M C00A C00H 121.9(4) . . ?
C00M C00A C00S 118.2(4) . . ?
C00S C00A C00H 119.9(3) . . ?
O003 C00B C00E 107.3(4) . . ?
O005 C00B O003 120.9(4) . . ?
O005 C00B C00E 131.8(4) . . ?
O003 C00C C008 104.0(3) . . ?
O003 C00C C00I 107.8(3) . . ?
O003 C00C C00O 109.3(3) . . ?
C008 C00C C00I 106.1(3) . . ?
C00O C00C C008 115.2(3) . . ?
C00O C00C C00I 113.7(4) . . ?
O004 C00D C00E 110.6(4) . . ?
O007 C00D O004 124.8(4) . . ?
O007 C00D C00E 124.6(4) . . ?
C008 C00E C00B 109.5(4) . . ?
C008 C00E C00D 128.8(4) . . ?
C00B C00E C00D 121.6(4) . . ?
C00O C00F C00J 120.7(4) . . ?
C008 C00G C00H 114.8(3) . . ?
N006 C00H C00A 109.8(3) . . ?
N006 C00H C00G 113.9(3) . . ?
C00A C00H C00G 109.3(3) . . ?
O002 C00I C009 104.0(3) . . ?
O002 C00I C00C 108.1(3) . . ?
C009 C00I C00C 114.7(4) . . ?
C00T C00J C00F 120.6(5) . . ?
C00S C00K C00N 119.1(4) . . ?
C00P C00L C00O 120.9(4) . . ?
C00R C00M C00A 121.6(5) . . ?
C00K C00N Br01 118.0(4) . . ?
C00R C00N Br01 120.7(3) . . ?
C00R C00N C00K 121.3(4) . . ?
C00F C00O C00C 120.9(4) . . ?
C00F C00O C00L 118.0(4) . . ?
C00L C00O C00C 121.0(4) . . ?
C00T C00P C00L 120.0(5) . . ?
C009 C00Q N006 112.1(4) . . ?
C009 C00Q C00Z 122.2(4) . . ?
C00Z C00Q N006 125.6(4) . . ?
C00N C00R C00M 118.6(4) . . ?
C00K C00S C00A 121.0(4) . . ?
C00P C00T C00J 119.7(5) . . ?
C00V C00U C00X 118.5(5) . . ?
C012 C00U C00V 118.5(5) . . ?
C012 C00U C00X 122.9(5) . . ?
C00Y C00V C00U 120.0(6) . . ?
C011 C00W C009 118.2(5) . . ?
O004 C00X C00U 105.7(4) . . ?
O004 C00X C010 107.0(4) . . ?
C010 C00X C00U 115.7(5) . . ?
C014 C00Y C00V 121.1(6) . . ?
C00Q C00Z C013 117.1(5) . . ?
C013 C011 C00W 121.1(5) . . ?
C00U C012 C015 120.5(5) . . ?
C011 C013 C00Z 121.3(5) . . ?
C00Y C014 C015 119.4(6) . . ?
C014 C015 C012 120.5(6) . . ?
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
Br01 C00N 1.897(4) . ?
O002 N006 1.479(5) . ?
O002 C00I 1.447(5) . ?
O003 C00B 1.381(5) . ?
O003 C00C 1.457(5) . ?
O004 C00D 1.329(6) . ?
O004 C00X 1.483(5) . ?
O005 C00B 1.192(5) . ?
N006 C00H 1.497(5) . ?
N006 C00Q 1.436(5) . ?
O007 C00D 1.191(5) . ?
C008 C00C 1.521(6) . ?
C008 C00E 1.341(6) . ?
C008 C00G 1.498(6) . ?
C009 C00I 1.493(7) . ?
C009 C00Q 1.376(6) . ?
C009 C00W 1.390(6) . ?
C00A C00H 1.517(5) . ?
C00A C00M 1.386(6) . ?
C00A C00S 1.393(6) . ?
C00B C00E 1.485(6) . ?
C00C C00I 1.566(6) . ?
C00C C00O 1.514(6) . ?
C00D C00E 1.493(6) . ?
C00F C00J 1.386(6) . ?
C00F C00O 1.385(6) . ?
C00G C00H 1.549(5) . ?
C00J C00T 1.375(7) . ?
C00K C00N 1.382(6) . ?
C00K C00S 1.377(6) . ?
C00L C00O 1.397(6) . ?
C00L C00P 1.386(7) . ?
C00M C00R 1.381(7) . ?
C00N C00R 1.379(7) . ?
C00P C00T 1.373(7) . ?
C00Q C00Z 1.383(7) . ?
C00U C00V 1.411(7) . ?
C00U C00X 1.516(7) . ?
C00U C012 1.370(7) . ?
C00V C00Y 1.381(8) . ?
C00W C011 1.386(8) . ?
C00X C010 1.510(7) . ?
C00Y C014 1.368(8) . ?
C00Z C013 1.392(8) . ?
C011 C013 1.374(8) . ?
C012 C015 1.400(8) . ?
C014 C015 1.372(8) . ?
