#------------------------------------------------------------------------------
#$Date: 2021-07-31 04:53:19 +0300 (Sat, 31 Jul 2021) $
#$Revision: 267843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564281.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_1564281
loop_
_publ_author_name
'Zhai, Yizhan'
'Zhang, Xue'
'Ma, Shengming'
_publ_section_title
;
 Stereoselective rhodium-catalyzed 2-C--H 1,3-dienylation of indoles: dual
 functions of the directing group
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02167B
_journal_year                    2021
_chemical_formula_moiety         'C23 H18 Br N3 O'
_chemical_formula_sum            'C23 H18 Br N3 O'
_chemical_formula_weight         432.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-04 deposited with the CCDC.	2021-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.198(4)
_cell_angle_beta                 91.243(4)
_cell_angle_gamma                108.491(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4828(5)
_cell_length_b                   7.7696(6)
_cell_length_c                   16.9566(12)
_cell_measurement_reflns_used    6086
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.86
_cell_measurement_theta_min      4.56
_cell_volume                     929.76(12)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9015
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.991
_diffrn_reflns_theta_min         4.563
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1691 before and 0.0925 after correction. The Ratio of minimum to maximum transmission is 0.6244. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.110
_refine_diff_density_min         -2.097
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0808
_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)+(0.1960P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2228
_refine_ls_wR_factor_ref         0.2407
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2968
_reflns_number_total             3490
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02167b2.cif
_cod_data_source_block           mj19656_0m
_cod_database_code               1564281
_shelx_shelxl_version_number     2016/6
_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   0.881
_shelx_estimated_absorpt_t_min   0.797
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22)
2.b X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Br1 Br 0.85069(8) 0.06498(6) 0.58843(3) 0.0375(3) Uani 1 1 d . . . . .
O1 O 1.0932(4) 0.2517(5) 0.00073(19) 0.0311(8) Uani 1 1 d . . . . .
N1 N 0.5548(5) 0.3419(5) 0.2051(2) 0.0220(8) Uani 1 1 d . . . . .
N2 N 0.2798(5) 0.1063(5) 0.1601(2) 0.0264(8) Uani 1 1 d . . . . .
N3 N 0.2828(5) 0.3098(5) 0.2745(2) 0.0285(9) Uani 1 1 d . . . . .
C1 C 0.4810(7) 0.7650(7) 0.2138(3) 0.0349(11) Uani 1 1 d . . . . .
H1A H 0.516172 0.694962 0.171733 0.042 Uiso 1 1 calc R . . . .
H1B H 0.423169 0.853170 0.202352 0.042 Uiso 1 1 calc R . . . .
C2 C 0.5127(6) 0.7396(6) 0.2887(3) 0.0292(10) Uani 1 1 d . . . . .
H2 H 0.475020 0.812864 0.328608 0.035 Uiso 1 1 calc R . . . .
C3 C 0.6008(6) 0.6084(6) 0.3156(3) 0.0239(9) Uani 1 1 d . . . . .
C4 C 0.6346(6) 0.6057(6) 0.3940(3) 0.0255(9) Uani 1 1 d . . . . .
H4 H 0.614030 0.701816 0.427343 0.031 Uiso 1 1 calc R . . . .
C5 C 0.6987(6) 0.4753(6) 0.4351(3) 0.0250(9) Uani 1 1 d . . . . .
C6 C 0.7570(6) 0.5232(6) 0.5154(3) 0.0262(9) Uani 1 1 d . . . . .
H6 H 0.763784 0.640546 0.539493 0.031 Uiso 1 1 calc R . . . .
C7 C 0.8050(6) 0.4025(6) 0.5603(3) 0.0291(10) Uani 1 1 d . . . . .
H7 H 0.845039 0.436554 0.614664 0.035 Uiso 1 1 calc R . . . .
C8 C 0.7936(6) 0.2328(6) 0.5250(3) 0.0266(9) Uani 1 1 d . . . . .
C9 C 0.7364(7) 0.1796(6) 0.4456(3) 0.0303(10) Uani 1 1 d . . . . .
H9 H 0.730510 0.062116 0.421980 0.036 Uiso 1 1 calc R . . . .
C10 C 0.6879(7) 0.3016(6) 0.4014(3) 0.0295(10) Uani 1 1 d . . . . .
H10 H 0.646654 0.266112 0.347274 0.035 Uiso 1 1 calc R . . . .
C11 C 0.6669(6) 0.4999(6) 0.2526(2) 0.0231(9) Uani 1 1 d . . . . .
C12 C 0.8458(6) 0.5493(6) 0.2276(2) 0.0251(9) Uani 1 1 d . . . . .
H12 H 0.948904 0.649882 0.250181 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8519(6) 0.4246(6) 0.1621(3) 0.0231(9) Uani 1 1 d . . . . .
C14 C 1.0018(6) 0.4198(6) 0.1132(3) 0.0245(9) Uani 1 1 d . . . . .
H14 H 1.122780 0.509636 0.121711 0.029 Uiso 1 1 calc R . . . .
C15 C 0.9655(6) 0.2790(6) 0.0526(2) 0.0246(9) Uani 1 1 d . . . . .
C16 C 0.7858(6) 0.1440(6) 0.0413(3) 0.0263(10) Uani 1 1 d . . . . .
H16 H 0.765933 0.046260 0.000703 0.032 Uiso 1 1 calc R . . . .
C17 C 0.6377(6) 0.1509(6) 0.0882(3) 0.0251(9) Uani 1 1 d . . . . .
H17 H 0.516588 0.061309 0.079597 0.030 Uiso 1 1 calc R . . . .
C18 C 0.6733(6) 0.2945(6) 0.1486(2) 0.0220(9) Uani 1 1 d . . . . .
C19 C 0.3626(6) 0.2477(6) 0.2140(2) 0.0217(9) Uani 1 1 d . . . . .
C20 C 0.0980(6) 0.0187(6) 0.1694(3) 0.0294(10) Uani 1 1 d . . . . .
H20 H 0.033742 -0.083301 0.132684 0.035 Uiso 1 1 calc R . . . .
C21 C -0.0007(7) 0.0696(6) 0.2300(3) 0.0280(10) Uani 1 1 d . . . . .
H21 H -0.129995 0.005731 0.236103 0.034 Uiso 1 1 calc R . . . .
C22 C 0.0995(6) 0.2182(6) 0.2811(3) 0.0285(10) Uani 1 1 d . . . . .
H22 H 0.035748 0.258265 0.323152 0.034 Uiso 1 1 calc R . . . .
C23 C 1.2767(7) 0.3833(7) 0.0076(3) 0.0304(10) Uani 1 1 d . . . . .
H23A H 1.354964 0.349234 -0.032640 0.046 Uiso 1 1 calc GR . . . .
H23B H 1.334290 0.387729 0.060482 0.046 Uiso 1 1 calc GR . . . .
H23C H 1.267219 0.503479 -0.000469 0.046 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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
C15 O1 C23 117.0(3) . . ?
C11 N1 C18 107.1(3) . . ?
C19 N1 C11 126.0(3) . . ?
C19 N1 C18 126.9(3) . . ?
C20 N2 C19 115.7(4) . . ?
C19 N3 C22 115.2(4) . . ?
H1A C1 H1B 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
C1 C2 H2 116.9 . . ?
C1 C2 C3 126.2(4) . . ?
C3 C2 H2 116.9 . . ?
C2 C3 C11 116.4(4) . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 C11 123.6(4) . . ?
C3 C4 H4 115.3 . . ?
C3 C4 C5 129.4(4) . . ?
C5 C4 H4 115.3 . . ?
C6 C5 C4 117.3(4) . . ?
C10 C5 C4 124.1(4) . . ?
C10 C5 C6 118.3(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(4) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 118.9(4) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 Br1 118.5(3) . . ?
C7 C8 C9 121.8(4) . . ?
C9 C8 Br1 119.7(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.6(4) . . ?
C10 C9 H9 120.7 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
N1 C11 C3 126.6(4) . . ?
C12 C11 N1 109.3(4) . . ?
C12 C11 C3 123.9(4) . . ?
C11 C12 H12 125.9 . . ?
C11 C12 C13 108.1(4) . . ?
C13 C12 H12 125.9 . . ?
C14 C13 C12 130.5(4) . . ?
C18 C13 C12 108.3(4) . . ?
C18 C13 C14 121.2(4) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.5(4) . . ?
C15 C14 H14 121.2 . . ?
O1 C15 C14 125.5(4) . . ?
O1 C15 C16 113.7(4) . . ?
C14 C15 C16 120.8(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 121.2 . . ?
C16 C17 C18 117.6(4) . . ?
C18 C17 H17 121.2 . . ?
C13 C18 N1 107.1(3) . . ?
C13 C18 C17 121.2(4) . . ?
C17 C18 N1 131.7(4) . . ?
N2 C19 N1 116.5(4) . . ?
N3 C19 N1 116.5(4) . . ?
N3 C19 N2 127.0(4) . . ?
N2 C20 H20 118.6 . . ?
N2 C20 C21 122.9(4) . . ?
C21 C20 H20 118.6 . . ?
C20 C21 H21 122.0 . . ?
C22 C21 C20 115.9(4) . . ?
C22 C21 H21 122.0 . . ?
N3 C22 C21 123.4(4) . . ?
N3 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 C8 1.904(5) . ?
O1 C15 1.365(5) . ?
O1 C23 1.423(6) . ?
N1 C11 1.413(5) . ?
N1 C18 1.421(5) . ?
N1 C19 1.410(5) . ?
N2 C19 1.337(6) . ?
N2 C20 1.334(6) . ?
N3 C19 1.328(5) . ?
N3 C22 1.342(6) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C1 C2 1.330(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.476(6) . ?
C3 C4 1.350(6) . ?
C3 C11 1.491(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.471(6) . ?
C5 C6 1.402(6) . ?
C5 C10 1.394(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(6) . ?
C8 C9 1.389(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.359(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.418(6) . ?
C13 C14 1.417(6) . ?
C13 C18 1.396(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(6) . ?
C15 C16 1.415(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(7) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
