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#$Date: 2022-12-15 11:54:28 +0200 (Thu, 15 Dec 2022) $
#$Revision: 279912 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106409.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_8106409
loop_
_publ_author_name
'Lu, Min'
'Li, Jianqing'
'Ma, Ling'
_publ_section_title
;
 Crystal structure of
 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1087
_journal_page_last               1088
_journal_paper_doi               10.1515/ncrs-2018-0209
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C12 H8 Br Cl O2'
_chemical_formula_weight         299.54
_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   mixed
_cell_angle_alpha                107.866(2)
_cell_angle_beta                 102.329(2)
_cell_angle_gamma                105.307(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3250(6)
_cell_length_b                   8.6187(6)
_cell_length_c                   9.9660(6)
_cell_measurement_reflns_used    5593
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      3.04
_cell_volume                     547.06(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7605
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.358
_diffrn_reflns_theta_min         3.044
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.980
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.531
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0487
_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)+(0.0398P)²+1.7718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2048
_reflns_number_total             2704
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0209_suppl.cif
_cod_data_source_block           Compound
_cod_database_code               8106409
_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   0.381
_shelx_estimated_absorpt_t_max   0.436
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
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 0.81338(7) 1.29058(6) 0.46369(5) 0.04682(17) Uani 1 1 d . . . . .
Cl1 Cl 0.8924(2) 0.88216(18) 0.78913(13) 0.0608(4) Uani 1 1 d . . . . .
O1 O 0.5469(4) 0.9388(4) 0.2243(3) 0.0392(7) Uani 1 1 d . . . . .
O2 O 0.1247(5) 0.3529(4) -0.0550(4) 0.0542(9) Uani 1 1 d . . . . .
C1 C 0.7951(6) 0.8976(6) 0.6203(5) 0.0403(10) Uani 1 1 d . . . . .
C2 C 0.8367(6) 1.0591(6) 0.6111(5) 0.0392(9) Uani 1 1 d . . . . .
H2 H 0.918191 1.159400 0.694007 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7559(6) 1.0698(5) 0.4773(5) 0.0356(9) Uani 1 1 d . . . . .
C4 C 0.6333(6) 0.9209(5) 0.3517(4) 0.0333(8) Uani 1 1 d . . . . .
C5 C 0.5920(6) 0.7572(5) 0.3641(4) 0.0351(9) Uani 1 1 d . . . . .
C6 C 0.6748(6) 0.7478(6) 0.4985(5) 0.0400(10) Uani 1 1 d . . . . .
H6 H 0.649223 0.640036 0.506689 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4449(6) 0.6073(5) 0.2371(4) 0.0372(9) Uani 1 1 d . . . . .
H7 H 0.391793 0.501683 0.245968 0.045 Uiso 1 1 calc R U . . .
C8 C 0.3879(6) 0.6240(5) 0.1085(5) 0.0379(9) Uani 1 1 d . . . . .
C9 C 0.4826(8) 0.7888(6) 0.0887(5) 0.0457(11) Uani 1 1 d . . . . .
C10 C 0.3210(8) 0.7917(6) -0.0327(5) 0.0522(12) Uani 1 1 d . . . . .
H10A H 0.379139 0.851487 -0.090018 0.063 Uiso 1 1 calc R U . . .
H10B H 0.237855 0.850128 0.009296 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1987(7) 0.5998(6) -0.1305(5) 0.0456(11) Uani 1 1 d . . . . .
H11A H 0.059265 0.583703 -0.171254 0.055 Uiso 1 1 calc R U . . .
H11B H 0.249057 0.559157 -0.212070 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2221(6) 0.5025(5) -0.0295(4) 0.0388(9) Uani 1 1 d . . . . .
H9 H 0.619(8) 0.788(7) 0.051(6) 0.068(17) Uiso 1 1 d . . . . .
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'
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
C4 O1 C9 116.3(3) . .
C6 C1 C2 121.2(4) . .
C6 C1 Cl1 119.1(3) . .
C2 C1 Cl1 119.7(3) . .
C1 C2 C3 119.1(4) . .
C1 C2 H2 120.4 . .
C3 C2 H2 120.4 . .
C2 C3 C4 121.3(4) . .
C2 C3 Br1 119.3(3) . .
C4 C3 Br1 119.3(3) . .
O1 C4 C3 119.2(4) . .
O1 C4 C5 122.2(3) . .
C3 C4 C5 118.5(4) . .
C6 C5 C4 119.8(4) . .
C6 C5 C7 122.8(4) . .
C4 C5 C7 117.1(4) . .
C1 C6 C5 120.2(4) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C8 C7 C5 118.7(4) . .
C8 C7 H7 120.6 . .
C5 C7 H7 120.6 . .
C7 C8 C12 129.4(4) . .
C7 C8 C9 121.5(4) . .
C12 C8 C9 109.0(3) . .
O1 C9 C8 111.6(4) . .
O1 C9 C10 112.4(4) . .
C8 C9 C10 104.1(4) . .
O1 C9 H9 107(3) . .
C8 C9 H9 112(3) . .
C10 C9 H9 110(3) . .
C9 C10 C11 105.1(4) . .
C9 C10 H10A 110.7 . .
C11 C10 H10A 110.7 . .
C9 C10 H10B 110.7 . .
C11 C10 H10B 110.7 . .
H10A C10 H10B 108.8 . .
C12 C11 C10 105.6(3) . .
C12 C11 H11A 110.6 . .
C10 C11 H11A 110.6 . .
C12 C11 H11B 110.6 . .
C10 C11 H11B 110.6 . .
H11A C11 H11B 108.8 . .
O2 C12 C8 125.9(4) . .
O2 C12 C11 127.0(4) . .
C8 C12 C11 107.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.891(4) .
Cl1 C1 1.741(4) .
O1 C4 1.365(5) .
O1 C9 1.433(5) .
O2 C12 1.213(5) .
C1 C6 1.377(6) .
C1 C2 1.380(6) .
C2 C3 1.380(6) .
C2 H2 0.9300 .
C3 C4 1.395(5) .
C4 C5 1.412(6) .
C5 C6 1.384(6) .
C5 C7 1.453(5) .
C6 H6 0.9300 .
C7 C8 1.324(6) .
C7 H7 0.9300 .
C8 C12 1.482(5) .
C8 C9 1.499(6) .
C9 C10 1.513(6) .
C9 H9 1.14(6) .
C10 C11 1.531(6) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.505(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O2 1.14(6) 2.49(6) 3.449(7) 141(4) 2_665
C10 H10A O1 0.97 2.58 3.507(5) 161.2 2_675
C2 H2 O2 0.93 2.41 3.308(5) 161.8 1_666
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
C6 C1 C2 C3 0.0(7) . . . .
Cl1 C1 C2 C3 -178.9(3) . . . .
C1 C2 C3 C4 0.1(7) . . . .
C1 C2 C3 Br1 -179.7(3) . . . .
C9 O1 C4 C3 159.1(4) . . . .
C9 O1 C4 C5 -25.4(6) . . . .
C2 C3 C4 O1 176.0(4) . . . .
Br1 C3 C4 O1 -4.2(5) . . . .
C2 C3 C4 C5 0.3(6) . . . .
Br1 C3 C4 C5 -179.9(3) . . . .
O1 C4 C5 C6 -176.3(4) . . . .
C3 C4 C5 C6 -0.7(6) . . . .
O1 C4 C5 C7 -2.9(6) . . . .
C3 C4 C5 C7 172.7(4) . . . .
C2 C1 C6 C5 -0.4(7) . . . .
Cl1 C1 C6 C5 178.5(3) . . . .
C4 C5 C6 C1 0.8(7) . . . .
C7 C5 C6 C1 -172.2(4) . . . .
C6 C5 C7 C8 -173.5(4) . . . .
C4 C5 C7 C8 13.3(6) . . . .
C5 C7 C8 C12 -170.0(4) . . . .
C5 C7 C8 C9 4.6(7) . . . .
C4 O1 C9 C8 40.4(5) . . . .
C4 O1 C9 C10 157.0(4) . . . .
C7 C8 C9 O1 -31.3(6) . . . .
C12 C8 C9 O1 144.4(4) . . . .
C7 C8 C9 C10 -152.8(5) . . . .
C12 C8 C9 C10 22.8(5) . . . .
O1 C9 C10 C11 -151.4(4) . . . .
C8 C9 C10 C11 -30.4(5) . . . .
C9 C10 C11 C12 27.2(5) . . . .
C7 C8 C12 O2 -10.9(8) . . . .
C9 C8 C12 O2 173.9(5) . . . .
C7 C8 C12 C11 169.2(5) . . . .
C9 C8 C12 C11 -6.0(5) . . . .
C10 C11 C12 O2 166.9(5) . . . .
C10 C11 C12 C8 -13.2(5) . . . .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{3609a282-8c68-46ca-ab87-b723bee2f1dd} ? ? ?
{bf796a13-2a33-40f1-ac09-f8e5a7d666db} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{3609a282-8c68-46ca-ab87-b723bee2f1dd} '_publcif_info_datablock.publ_exptl'
{bf796a13-2a33-40f1-ac09-f8e5a7d666db} '_geom_hbond_atom_site_label_D'
loop_
_publcif_info_cif.paper_type
EE
