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#$Date: 2023-05-15 10:34:19 +0300 (Mon, 15 May 2023) $
#$Revision: 283764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107199.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_8107199
loop_
_publ_author_name
'Jiang, Dong-Li'
'Fan, Lian-Lian'
'Yin, Peng'
'Liang, Di'
'Li, Rui'
_publ_section_title
;
 Crystal structure of
 3-(3-bromophenyl)-1′,3′-dimethyl-2′H,3H,4H-spiro[furo[3,
 2-c]chromene-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)
 tetraone, C22H15BrN2O6
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              723
_journal_page_last               724
_journal_paper_doi               10.1515/ncrs-2022-0099
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C22 H15 Br N2 O6'
_chemical_formula_sum            'C22 H15 Br N2 O6'
_chemical_formula_weight         483.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 94.690(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1760(5)
_cell_length_b                   17.5652(19)
_cell_length_c                   21.734(2)
_cell_measurement_reflns_used    2293
_cell_measurement_temperature    170
_cell_measurement_theta_max      22.770
_cell_measurement_theta_min      2.209
_cell_volume                     1969.4(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18236
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.209
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.132
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0984 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.9229. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0569
_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)+(0.0289P)²+2.5579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2407
_reflns_number_total             4016
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0099_suppl.cif
_cod_data_source_block           0924j2_0m
_cod_original_cell_volume        1969.3(3)
_cod_original_sg_symbol_H-M      ' P 1 21/c 1'
_cod_database_code               8107199
_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   0.920
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C22(H22), C18(H18), C13(H13), C15(H15), C14(H14), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.91013(11) 0.59854(4) 0.05991(2) 0.0593(2) Uani 1 1 d . . . . .
O4 O 0.5038(5) 0.33479(16) 0.28634(11) 0.0213(7) Uani 1 1 d . . . . .
O3 O 0.3133(5) 0.37862(17) 0.17096(12) 0.0267(7) Uani 1 1 d . . . . .
O6 O 0.8550(6) 0.46066(17) 0.42791(12) 0.0274(7) Uani 1 1 d . . . . .
O2 O 0.9228(5) 0.24456(17) 0.29274(13) 0.0301(7) Uani 1 1 d . . . . .
O5 O 1.1097(6) 0.51329(19) 0.36196(13) 0.0331(8) Uani 1 1 d . . . . .
O1 O 0.9740(6) 0.2605(2) 0.08577(14) 0.0397(9) Uani 1 1 d . . . . .
N1 N 0.6628(6) 0.3301(2) 0.12743(14) 0.0235(8) Uani 1 1 d . . . . .
N2 N 0.9486(6) 0.2495(2) 0.18909(15) 0.0250(8) Uani 1 1 d . . . . .
C9 C 0.6137(7) 0.3746(3) 0.33611(17) 0.0213(10) Uani 1 1 d . . . . .
C8 C 0.8085(7) 0.4206(2) 0.32313(17) 0.0197(9) Uani 1 1 d . . . . .
C5 C 0.6807(7) 0.3431(2) 0.23910(17) 0.0202(9) Uani 1 1 d . . . . .
C17 C 0.7447(7) 0.4880(2) 0.22013(17) 0.0192(9) Uani 1 1 d . . . . .
C10 C 0.9391(8) 0.4679(3) 0.36914(18) 0.0246(10) Uani 1 1 d . . . . .
C4 C 0.8580(8) 0.2746(2) 0.24357(19) 0.0219(10) Uani 1 1 d . . . . .
C7 C 0.8452(7) 0.4176(2) 0.25530(16) 0.0186(9) Uani 1 1 d . . . . .
H7 H 1.031728 0.408755 0.248666 0.022 Uiso 1 1 calc R . . . .
C2 C 0.8703(8) 0.2795(3) 0.13116(19) 0.0255(10) Uani 1 1 d . . . . .
C6 C 0.5277(8) 0.3506(2) 0.17672(18) 0.0210(9) Uani 1 1 d . . . . .
C12 C 0.6603(8) 0.4112(3) 0.44131(18) 0.0257(10) Uani 1 1 d . . . . .
C11 C 0.5260(8) 0.3661(2) 0.39639(18) 0.0217(9) Uani 1 1 d . . . . .
C16 C 0.3250(8) 0.3185(3) 0.41299(19) 0.0273(10) Uani 1 1 d . . . . .
H16 H 0.232650 0.287497 0.382877 0.033 Uiso 1 1 calc R . . . .
C22 C 0.8560(8) 0.5089(3) 0.16667(18) 0.0265(10) Uani 1 1 d . . . . .
H22 H 0.999581 0.481366 0.153503 0.032 Uiso 1 1 calc R . . . .
C18 C 0.5309(8) 0.5282(3) 0.2385(2) 0.0272(10) Uani 1 1 d . . . . .
H18 H 0.451822 0.513726 0.274650 0.033 Uiso 1 1 calc R . . . .
C21 C 0.7556(9) 0.5701(3) 0.1329(2) 0.0333(12) Uani 1 1 d . . . . .
C13 C 0.6007(9) 0.4086(3) 0.50256(19) 0.0351(12) Uani 1 1 d . . . . .
H13 H 0.695206 0.438125 0.533336 0.042 Uiso 1 1 calc R . . . .
C15 C 0.2637(9) 0.3174(3) 0.4731(2) 0.0336(11) Uani 1 1 d . . . . .
H15 H 0.126434 0.285854 0.484591 0.040 Uiso 1 1 calc R . . . .
C14 C 0.4008(10) 0.3619(3) 0.5173(2) 0.0381(12) Uani 1 1 d . . . . .
H14 H 0.355698 0.360206 0.558824 0.046 Uiso 1 1 calc R . . . .
C1 C 0.5597(9) 0.3546(3) 0.06500(18) 0.0359(12) Uani 1 1 d . . . . .
H1A H 0.697071 0.351296 0.036641 0.054 Uiso 1 1 calc GR . . . .
H1B H 0.498530 0.407307 0.066716 0.054 Uiso 1 1 calc GR . . . .
H1C H 0.415283 0.321466 0.050316 0.054 Uiso 1 1 calc GR . . . .
C19 C 0.4352(9) 0.5897(3) 0.2034(2) 0.0377(12) Uani 1 1 d . . . . .
H19 H 0.290348 0.617094 0.216046 0.045 Uiso 1 1 calc R . . . .
C20 C 0.5457(9) 0.6119(3) 0.1505(2) 0.0405(13) Uani 1 1 d . . . . .
H20 H 0.480472 0.654320 0.126947 0.049 Uiso 1 1 calc R . . . .
C3 C 1.1454(9) 0.1890(3) 0.1919(2) 0.0405(13) Uani 1 1 d . . . . .
H3A H 1.229580 0.185786 0.233879 0.061 Uiso 1 1 calc GR . . . .
H3B H 1.275573 0.200544 0.162937 0.061 Uiso 1 1 calc GR . . . .
H3C H 1.062344 0.140199 0.180734 0.061 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 0.0033 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
C9 O4 C5 105.3(3) . .
C12 O6 C10 122.8(3) . .
C2 N1 C1 117.3(3) . .
C6 N1 C2 124.2(3) . .
C6 N1 C1 118.0(3) . .
C4 N2 C2 124.1(4) . .
C4 N2 C3 118.5(4) . .
C2 N2 C3 117.4(4) . .
O4 C9 C11 121.8(4) . .
C8 C9 O4 114.3(3) . .
C8 C9 C11 123.8(4) . .
C9 C8 C10 121.7(4) . .
C9 C8 C7 110.1(3) . .
C10 C8 C7 128.1(4) . .
O4 C5 C4 107.0(3) . .
O4 C5 C7 106.7(3) . .
O4 C5 C6 109.3(3) . .
C4 C5 C7 109.3(3) . .
C4 C5 C6 113.3(3) . .
C6 C5 C7 111.0(3) . .
C22 C17 C7 119.2(4) . .
C22 C17 C18 119.8(4) . .
C18 C17 C7 120.9(4) . .
O6 C10 C8 115.2(4) . .
O5 C10 O6 117.8(4) . .
O5 C10 C8 127.1(4) . .
O2 C4 N2 121.8(4) . .
O2 C4 C5 121.7(4) . .
N2 C4 C5 116.5(3) . .
C8 C7 C5 98.0(3) . .
C8 C7 C17 113.5(3) . .
C17 C7 C5 113.8(3) . .
O1 C2 N1 121.4(4) . .
O1 C2 N2 121.2(4) . .
N1 C2 N2 117.4(4) . .
O3 C6 N1 123.1(4) . .
O3 C6 C5 122.3(4) . .
N1 C6 C5 114.3(3) . .
O6 C12 C11 122.7(4) . .
O6 C12 C13 116.5(4) . .
C13 C12 C11 120.9(4) . .
C12 C11 C9 113.9(4) . .
C12 C11 C16 119.6(4) . .
C16 C11 C9 126.5(4) . .
C15 C16 C11 119.2(4) . .
C21 C22 C17 119.2(4) . .
C19 C18 C17 119.4(4) . .
C22 C21 Br1 118.9(4) . .
C22 C21 C20 122.2(4) . .
C20 C21 Br1 118.9(4) . .
C14 C13 C12 118.2(4) . .
C16 C15 C14 120.5(4) . .
C13 C14 C15 121.6(4) . .
C20 C19 C18 121.5(5) . .
C19 C20 C21 117.8(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C21 1.900(5) .
O4 C9 1.372(5) .
O4 C5 1.438(4) .
O3 C6 1.211(5) .
O6 C10 1.389(5) .
O6 C12 1.379(5) .
O2 C4 1.214(5) .
O5 C10 1.210(5) .
O1 C2 1.208(5) .
N1 C2 1.391(5) .
N1 C6 1.374(5) .
N1 C1 1.481(5) .
N2 C4 1.381(5) .
N2 C2 1.394(5) .
N2 C3 1.471(6) .
C9 C8 1.340(6) .
C9 C11 1.429(6) .
C8 C10 1.427(6) .
C8 C7 1.503(5) .
C5 C4 1.512(6) .
C5 C7 1.584(6) .
C5 C6 1.519(5) .
C17 C7 1.522(5) .
C17 C22 1.388(6) .
C17 C18 1.399(6) .
C12 C11 1.397(6) .
C12 C13 1.392(6) .
C11 C16 1.405(6) .
C16 C15 1.369(6) .
C22 C21 1.380(6) .
C18 C19 1.390(6) .
C21 C20 1.390(7) .
C13 C14 1.378(7) .
C15 C14 1.390(6) .
C19 C20 1.381(7) .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{c19bd218-336c-4bea-9f29-c0b076a9b343} ? ? ?
{ab219671-691e-4a27-96d5-e218555a7c41} 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
{c19bd218-336c-4bea-9f29-c0b076a9b343} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EE
