#------------------------------------------------------------------------------
#$Date: 2022-07-29 00:54:16 +0300 (Fri, 29 Jul 2022) $
#$Revision: 276980 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/04/7130434.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_7130434
loop_
_publ_author_name
'Chen, Chao'
'Liu, Ru-Xin'
'Xiong, Feng'
'Li, Zi-Hao'
'Kang, Jun-Chen'
'Ding, Tong-Mei'
'Zhang, Shu-Yu'
_publ_section_title
;
 Electrochemical collective synthesis of labeled pyrroloindoline alkaloids
 with Freon-type methanes as functional C1 synthons
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03301A
_journal_year                    2022
_chemical_formula_moiety         'C12 H12 Br Cl2 N O'
_chemical_formula_sum            'C12 H12 Br Cl2 N O'
_chemical_formula_weight         337.04
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-14 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                107.939(9)
_cell_angle_beta                 94.991(8)
_cell_angle_gamma                110.518(14)
_cell_formula_units_Z            4
_cell_length_a                   8.4386(17)
_cell_length_b                   11.633(2)
_cell_length_c                   15.457(2)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      4.32
_cell_volume                     1319.3(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15101
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.332
_diffrn_reflns_theta_min         4.327
_exptl_absorpt_coefficient_mu    7.836
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6023
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0312
_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)+(0.0450P)²+1.1126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4321
_reflns_number_total             4784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03301a2.cif
_cod_data_source_block           t_a
_cod_database_code               7130434
_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_min   0.367
_shelx_estimated_absorpt_t_max   0.407
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 0.42677(4) 0.26751(3) 0.60558(2) 0.04160(11) Uani 1 1 d . . . . .
C1 C 0.7532(3) 0.6533(2) 0.77015(17) 0.0236(5) Uani 1 1 d . . . . .
O1 O 0.7145(3) 0.65239(19) 0.99052(12) 0.0366(4) Uani 1 1 d . . . . .
N1 N 0.7934(3) 0.7129(2) 0.86752(14) 0.0266(4) Uani 1 1 d . . . . .
Cl1 Cl 0.86986(11) 0.30145(9) 0.91459(6) 0.0549(2) Uani 1 1 d . . . . .
Cl3 Cl 0.17483(10) 0.51266(6) 0.62697(5) 0.04174(17) Uani 1 1 d . . . . .
C3 C 0.7580(3) 0.6320(3) 0.61321(19) 0.0320(6) Uani 1 1 d . . . . .
H3 H 0.798276 0.668554 0.568202 0.038 Uiso 1 1 calc R U . . .
Br2 Br 0.16112(4) 0.83041(3) 0.49993(2) 0.03946(10) Uani 1 1 d . . . . .
C2 C 0.8137(3) 0.7116(3) 0.70731(18) 0.0287(5) Uani 1 1 d . . . . .
H2 H 0.889745 0.801841 0.727412 0.034 Uiso 1 1 calc R U . . .
O2 O 0.6361(3) 0.9608(2) 0.85139(15) 0.0415(5) Uani 1 1 d . . . . .
N2 N 0.4324(3) 1.0503(2) 0.85203(15) 0.0284(4) Uani 1 1 d . . . . .
Cl2 Cl 0.89837(11) 0.37799(9) 0.75432(7) 0.0540(2) Uani 1 1 d . . . . .
Cl4 Cl 0.22441(9) 0.71940(7) 0.80462(5) 0.03688(16) Uani 1 1 d . . . . .
C4 C 0.6454(3) 0.5011(3) 0.58368(18) 0.0311(6) Uani 1 1 d . . . . .
H4 H 0.609871 0.448277 0.519192 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6382(3) 0.5217(2) 0.74298(16) 0.0230(5) Uani 1 1 d . . . . .
C5 C 0.5844(3) 0.4471(2) 0.64937(17) 0.0272(5) Uani 1 1 d . . . . .
C9 C 0.9123(3) 0.8477(3) 0.91993(19) 0.0334(6) Uani 1 1 d . . . . .
H9A H 1.024415 0.863359 0.902074 0.050 Uiso 1 1 calc R U . . .
H9B H 0.927897 0.863204 0.986719 0.050 Uiso 1 1 calc R U . . .
H9C H 0.865007 0.907706 0.906490 0.050 Uiso 1 1 calc R U . . .
C8 C 0.7058(3) 0.6272(2) 0.90717(17) 0.0266(5) Uani 1 1 d . . . . .
C7 C 0.5945(3) 0.4941(2) 0.82958(17) 0.0243(5) Uani 1 1 d . . . . .
C10 C 0.4025(3) 0.4650(3) 0.83286(19) 0.0324(6) Uani 1 1 d . . . . .
H10A H 0.373403 0.535664 0.824009 0.049 Uiso 1 1 calc R U . . .
H10B H 0.383610 0.459740 0.893456 0.049 Uiso 1 1 calc R U . . .
H10C H 0.328521 0.380971 0.783215 0.049 Uiso 1 1 calc R U . . .
C11 C 0.6407(3) 0.3865(2) 0.85024(18) 0.0279(5) Uani 1 1 d . . . . .
H11A H 0.604949 0.379553 0.908386 0.034 Uiso 1 1 calc R U . . .
H11B H 0.571615 0.301080 0.799240 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8308(4) 0.4081(3) 0.8607(2) 0.0366(6) Uani 1 1 d . . . . .
H12 H 0.902590 0.501474 0.902243 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2990(3) 1.0413(2) 0.78606(17) 0.0239(5) Uani 1 1 d . . . . .
C14 C 0.1858(3) 1.1041(2) 0.80226(19) 0.0281(5) Uani 1 1 d . . . . .
H14 H 0.190410 1.159508 0.863027 0.034 Uiso 1 1 calc R U . . .
C15 C 0.0653(3) 1.0819(3) 0.7252(2) 0.0312(6) Uani 1 1 d . . . . .
H15 H -0.013919 1.123620 0.733721 0.037 Uiso 1 1 calc R U . . .
C16 C 0.0572(3) 1.0012(3) 0.63668(19) 0.0308(5) Uani 1 1 d . . . . .
H16 H -0.027020 0.987164 0.585353 0.037 Uiso 1 1 calc R U . . .
C17 C 0.1739(3) 0.9402(2) 0.62324(17) 0.0266(5) Uani 1 1 d . . . . .
C18 C 0.2967(3) 0.9599(2) 0.69735(17) 0.0241(5) Uani 1 1 d . . . . .
C19 C 0.4435(3) 0.9148(2) 0.70499(18) 0.0269(5) Uani 1 1 d . . . . .
C20 C 0.5178(3) 0.9744(3) 0.81079(19) 0.0306(5) Uani 1 1 d . . . . .
C21 C 0.4627(4) 1.1170(3) 0.95210(19) 0.0369(6) Uani 1 1 d . . . . .
H21A H 0.461863 1.204754 0.965120 0.055 Uiso 1 1 calc R U . . .
H21B H 0.575554 1.125652 0.982182 0.055 Uiso 1 1 calc R U . . .
H21C H 0.371170 1.065772 0.976466 0.055 Uiso 1 1 calc R U . . .
C22 C 0.5875(4) 0.9776(3) 0.6585(2) 0.0372(6) Uani 1 1 d . . . . .
H22A H 0.541568 0.946741 0.591343 0.056 Uiso 1 1 calc R U . . .
H22B H 0.684507 0.952283 0.669458 0.056 Uiso 1 1 calc R U . . .
H22C H 0.628075 1.073713 0.685267 0.056 Uiso 1 1 calc R U . . .
C23 C 0.3924(3) 0.7647(2) 0.66703(18) 0.0286(5) Uani 1 1 d . . . . .
H23A H 0.386826 0.735488 0.599114 0.034 Uiso 1 1 calc R U . . .
H23B H 0.485355 0.746158 0.696054 0.034 Uiso 1 1 calc R U . . .
C24 C 0.2220(3) 0.6832(2) 0.68334(18) 0.0287(5) Uani 1 1 d . . . . .
H24 H 0.128286 0.703290 0.655226 0.034 Uiso 1 1 calc R U . . .
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'
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'
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 C1 C6 123.1(2) . . ?
C2 C1 N1 127.1(2) . . ?
C6 C1 N1 109.9(2) . . ?
C8 N1 C1 111.2(2) . . ?
C8 N1 C9 123.9(2) . . ?
C1 N1 C9 124.9(2) . . ?
C4 C3 C2 121.6(2) . . ?
C1 C2 C3 117.0(2) . . ?
C20 N2 C13 110.9(2) . . ?
C20 N2 C21 124.0(2) . . ?
C13 N2 C21 124.7(2) . . ?
C3 C4 C5 119.5(2) . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 C7 133.4(2) . . ?
C1 C6 C7 108.4(2) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 Br1 121.18(19) . . ?
C4 C5 Br1 118.08(19) . . ?
O1 C8 N1 125.5(2) . . ?
O1 C8 C7 125.8(2) . . ?
N1 C8 C7 108.7(2) . . ?
C6 C7 C8 101.81(19) . . ?
C6 C7 C10 112.2(2) . . ?
C8 C7 C10 107.9(2) . . ?
C6 C7 C11 117.5(2) . . ?
C8 C7 C11 108.3(2) . . ?
C10 C7 C11 108.6(2) . . ?
C12 C11 C7 115.7(2) . . ?
C11 C12 Cl2 113.7(2) . . ?
C11 C12 Cl1 109.19(19) . . ?
Cl2 C12 Cl1 108.28(15) . . ?
C14 C13 C18 123.1(2) . . ?
C14 C13 N2 127.1(2) . . ?
C18 C13 N2 109.8(2) . . ?
C13 C14 C15 116.8(2) . . ?
C16 C15 C14 122.0(2) . . ?
C15 C16 C17 119.5(2) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 Br2 120.77(19) . . ?
C16 C17 Br2 118.52(19) . . ?
C17 C18 C13 117.9(2) . . ?
C17 C18 C19 133.3(2) . . ?
C13 C18 C19 108.7(2) . . ?
C18 C19 C20 101.8(2) . . ?
C18 C19 C23 116.1(2) . . ?
C20 C19 C23 111.1(2) . . ?
C18 C19 C22 111.8(2) . . ?
C20 C19 C22 107.4(2) . . ?
C23 C19 C22 108.2(2) . . ?
O2 C20 N2 125.3(3) . . ?
O2 C20 C19 126.1(2) . . ?
N2 C20 C19 108.6(2) . . ?
C24 C23 C19 115.5(2) . . ?
C23 C24 Cl3 109.51(17) . . ?
C23 C24 Cl4 112.00(18) . . ?
Cl3 C24 Cl4 109.79(14) . . ?
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 C5 1.902(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.397(3) . ?
C1 N1 1.402(3) . ?
O1 C8 1.220(3) . ?
N1 C8 1.361(3) . ?
N1 C9 1.447(3) . ?
Cl1 C12 1.794(3) . ?
Cl3 C24 1.782(3) . ?
C3 C4 1.383(4) . ?
C3 C2 1.393(4) . ?
Br2 C17 1.909(3) . ?
O2 C20 1.216(3) . ?
N2 C20 1.372(3) . ?
N2 C13 1.404(3) . ?
N2 C21 1.454(3) . ?
Cl2 C12 1.761(3) . ?
Cl4 C24 1.787(3) . ?
C4 C5 1.395(4) . ?
C6 C5 1.374(4) . ?
C6 C7 1.516(3) . ?
C8 C7 1.536(3) . ?
C7 C10 1.544(3) . ?
C7 C11 1.545(3) . ?
C11 C12 1.520(4) . ?
C13 C14 1.388(3) . ?
C13 C18 1.400(3) . ?
C14 C15 1.392(4) . ?
C15 C16 1.380(4) . ?
C16 C17 1.397(4) . ?
C17 C18 1.380(3) . ?
C18 C19 1.513(3) . ?
C19 C20 1.538(4) . ?
C19 C23 1.541(3) . ?
C19 C22 1.543(4) . ?
C23 C24 1.512(4) . ?
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
C2 C1 N1 C8 177.9(2) . . . . ?
C6 C1 N1 C8 -1.7(3) . . . . ?
C2 C1 N1 C9 -2.1(4) . . . . ?
C6 C1 N1 C9 178.3(2) . . . . ?
C6 C1 C2 C3 -1.5(4) . . . . ?
N1 C1 C2 C3 178.9(2) . . . . ?
C4 C3 C2 C1 0.9(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
N1 C1 C6 C5 -179.8(2) . . . . ?
C2 C1 C6 C7 -177.5(2) . . . . ?
N1 C1 C6 C7 2.1(3) . . . . ?
C1 C6 C5 C4 1.0(4) . . . . ?
C7 C6 C5 C4 178.5(2) . . . . ?
C1 C6 C5 Br1 -179.53(17) . . . . ?
C7 C6 C5 Br1 -2.1(4) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
C3 C4 C5 Br1 178.94(19) . . . . ?
C1 N1 C8 O1 -179.4(2) . . . . ?
C9 N1 C8 O1 0.6(4) . . . . ?
C1 N1 C8 C7 0.5(3) . . . . ?
C9 N1 C8 C7 -179.4(2) . . . . ?
C5 C6 C7 C8 -179.4(3) . . . . ?
C1 C6 C7 C8 -1.7(2) . . . . ?
C5 C6 C7 C10 -64.2(3) . . . . ?
C1 C6 C7 C10 113.4(2) . . . . ?
C5 C6 C7 C11 62.6(4) . . . . ?
C1 C6 C7 C11 -119.8(2) . . . . ?
O1 C8 C7 C6 -179.4(2) . . . . ?
N1 C8 C7 C6 0.7(2) . . . . ?
O1 C8 C7 C10 62.4(3) . . . . ?
N1 C8 C7 C10 -117.5(2) . . . . ?
O1 C8 C7 C11 -54.9(3) . . . . ?
N1 C8 C7 C11 125.1(2) . . . . ?
C6 C7 C11 C12 58.1(3) . . . . ?
C8 C7 C11 C12 -56.4(3) . . . . ?
C10 C7 C11 C12 -173.3(2) . . . . ?
C7 C11 C12 Cl2 -74.5(3) . . . . ?
C7 C11 C12 Cl1 164.47(18) . . . . ?
C20 N2 C13 C14 179.9(2) . . . . ?
C21 N2 C13 C14 7.1(4) . . . . ?
C20 N2 C13 C18 -1.5(3) . . . . ?
C21 N2 C13 C18 -174.3(2) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
N2 C13 C14 C15 178.9(2) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C15 C16 C17 Br2 -179.42(19) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
Br2 C17 C18 C13 -179.87(17) . . . . ?
C16 C17 C18 C19 -176.5(2) . . . . ?
Br2 C17 C18 C19 3.0(4) . . . . ?
C14 C13 C18 C17 -1.0(4) . . . . ?
N2 C13 C18 C17 -179.6(2) . . . . ?
C14 C13 C18 C19 176.8(2) . . . . ?
N2 C13 C18 C19 -1.8(3) . . . . ?
C17 C18 C19 C20 -178.7(3) . . . . ?
C13 C18 C19 C20 3.9(3) . . . . ?
C17 C18 C19 C23 -57.9(4) . . . . ?
C13 C18 C19 C23 124.8(2) . . . . ?
C17 C18 C19 C22 66.9(4) . . . . ?
C13 C18 C19 C22 -110.4(2) . . . . ?
C13 N2 C20 O2 -178.1(3) . . . . ?
C21 N2 C20 O2 -5.2(4) . . . . ?
C13 N2 C20 C19 4.1(3) . . . . ?
C21 N2 C20 C19 177.0(2) . . . . ?
C18 C19 C20 O2 177.4(3) . . . . ?
C23 C19 C20 O2 53.1(4) . . . . ?
C22 C19 C20 O2 -65.1(3) . . . . ?
C18 C19 C20 N2 -4.8(3) . . . . ?
C23 C19 C20 N2 -129.1(2) . . . . ?
C22 C19 C20 N2 112.7(2) . . . . ?
C18 C19 C23 C24 -37.1(3) . . . . ?
C20 C19 C23 C24 78.6(3) . . . . ?
C22 C19 C23 C24 -163.7(2) . . . . ?
C19 C23 C24 Cl3 175.23(18) . . . . ?
C19 C23 C24 Cl4 -62.7(3) . . . . ?
