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#$Date: 2022-08-18 00:58:25 +0300 (Thu, 18 Aug 2022) $
#$Revision: 277284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/05/7130545.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_7130545
loop_
_publ_author_name
'Yan, Sheng-Jiao'
'Chen, Li'
'Li, Yuan-Da'
'Lv, Ying'
'Lu, Zi-Han'
_publ_section_title
;
 Cu-Catalyzed Decarboxylative Annulation of N-Substituted Glycines with
 3-Formylchromones: Synthesis of Functionalized
 Chromeno[2,3-b]pyrrol-4(1H)-ones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03816A
_journal_year                    2022
_chemical_formula_sum            'C18 H12 Cl N O3'
_chemical_formula_weight         325.74
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-26 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.261(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6982(9)
_cell_length_b                   12.4059(8)
_cell_length_c                   7.6199(5)
_cell_measurement_reflns_used    8749
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      27.9379
_cell_measurement_theta_min      2.6371
_cell_volume                     1460.24(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301(2)
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33858
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.139
_diffrn_reflns_theta_max         25.139
_diffrn_reflns_theta_min         2.105
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0437
_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)+(0.0697P)²+0.5156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2004
_reflns_number_total             2607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03816a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130545
_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   0.927
_shelx_estimated_absorpt_t_max   0.952
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
Cl1 Cl 0.35319(4) 0.17398(6) 0.74260(10) 0.0639(3) Uani 1 1 d . . . . .
N1 N 0.81444(12) 0.33540(15) 0.5391(3) 0.0459(5) Uani 1 1 d . . . . .
O1 O 0.67564(10) 0.36401(12) 0.6028(2) 0.0459(4) Uani 1 1 d . . . . .
O2 O 0.65214(12) 0.03021(13) 0.5895(3) 0.0614(5) Uani 1 1 d . . . . .
O3 O 0.92557(12) 0.76020(15) 0.6404(3) 0.0653(5) Uani 1 1 d . . . . .
C1 C 0.44903(15) 0.2280(2) 0.6976(3) 0.0472(6) Uani 1 1 d . . . . .
C2 C 0.46051(16) 0.3393(2) 0.7039(3) 0.0498(6) Uani 1 1 d . . . . .
H2 H 0.417251 0.384153 0.731158 0.060 Uiso 1 1 calc R U . . .
C3 C 0.53651(15) 0.3819(2) 0.6693(3) 0.0481(6) Uani 1 1 d . . . . .
H3 H 0.544740 0.456126 0.670652 0.058 Uiso 1 1 calc R U . . .
C4 C 0.60088(14) 0.31355(17) 0.6323(3) 0.0407(5) Uani 1 1 d . . . . .
C5 C 0.59064(14) 0.20235(18) 0.6259(3) 0.0414(5) Uani 1 1 d . . . . .
C6 C 0.51193(15) 0.16061(19) 0.6582(3) 0.0448(5) Uani 1 1 d . . . . .
H6 H 0.502418 0.086597 0.652806 0.054 Uiso 1 1 calc R U . . .
C7 C 0.65999(15) 0.12913(19) 0.5885(3) 0.0450(5) Uani 1 1 d . . . . .
C8 C 0.73501(15) 0.18612(18) 0.5563(3) 0.0440(5) Uani 1 1 d . . . . .
C9 C 0.73733(14) 0.29648(19) 0.5671(3) 0.0422(5) Uani 1 1 d . . . . .
C10 C 0.81734(17) 0.1555(2) 0.5166(4) 0.0549(6) Uani 1 1 d . . . . .
H10 H 0.835568 0.085571 0.499493 0.066 Uiso 1 1 calc R U . . .
C11 C 0.86361(17) 0.2458(2) 0.5083(4) 0.0557(7) Uani 1 1 d . . . . .
H11 H 0.919839 0.248308 0.485507 0.067 Uiso 1 1 calc R U . . .
C12 C 0.84257(14) 0.44512(19) 0.5575(3) 0.0447(5) Uani 1 1 d . . . . .
C13 C 0.78876(16) 0.5268(2) 0.4839(3) 0.0532(6) Uani 1 1 d . . . . .
H13 H 0.734807 0.510596 0.416755 0.064 Uiso 1 1 calc R U . . .
C14 C 0.81482(16) 0.6336(2) 0.5097(3) 0.0518(6) Uani 1 1 d . . . . .
H14 H 0.777917 0.688877 0.461461 0.062 Uiso 1 1 calc R U . . .
C15 C 0.89515(15) 0.6575(2) 0.6064(3) 0.0485(6) Uani 1 1 d . . . . .
C16 C 0.94992(16) 0.5747(2) 0.6765(4) 0.0578(7) Uani 1 1 d . . . . .
H16 H 1.004917 0.590551 0.739130 0.069 Uiso 1 1 calc R U . . .
C17 C 0.92345(15) 0.4694(2) 0.6539(4) 0.0531(6) Uani 1 1 d . . . . .
H17 H 0.960053 0.414233 0.703612 0.064 Uiso 1 1 calc R U . . .
C18 C 0.8680(2) 0.8462(2) 0.5790(4) 0.0696(8) Uani 1 1 d . . . . .
H18A H 0.853886 0.844228 0.451181 0.104 Uiso 1 1 calc R U . . .
H18B H 0.895228 0.913672 0.616419 0.104 Uiso 1 1 calc R U . . .
H18C H 0.816050 0.838664 0.627983 0.104 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 0.0033 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'
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'
Cl Cl 0.1484 0.1585 '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
C9 N1 C11 106.2(2) . . ?
C9 N1 C12 126.35(19) . . ?
C11 N1 C12 127.1(2) . . ?
C9 O1 C4 114.42(17) . . ?
C15 O3 C18 117.1(2) . . ?
C6 C1 C2 121.3(2) . . ?
C6 C1 Cl1 119.5(2) . . ?
C2 C1 Cl1 119.16(19) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O1 C4 C3 115.3(2) . . ?
O1 C4 C5 122.7(2) . . ?
C3 C4 C5 122.0(2) . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 C7 122.0(2) . . ?
C6 C5 C7 120.5(2) . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O2 C7 C8 125.3(2) . . ?
O2 C7 C5 122.0(2) . . ?
C8 C7 C5 112.6(2) . . ?
C9 C8 C10 105.2(2) . . ?
C9 C8 C7 119.8(2) . . ?
C10 C8 C7 135.0(2) . . ?
O1 C9 N1 120.4(2) . . ?
O1 C9 C8 128.4(2) . . ?
N1 C9 C8 111.2(2) . . ?
C11 C10 C8 107.8(2) . . ?
C11 C10 H10 126.1 . . ?
C8 C10 H10 126.1 . . ?
C10 C11 N1 109.6(2) . . ?
C10 C11 H11 125.2 . . ?
N1 C11 H11 125.2 . . ?
C13 C12 C17 119.8(2) . . ?
C13 C12 N1 120.4(2) . . ?
C17 C12 N1 119.9(2) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O3 C15 C14 123.9(2) . . ?
O3 C15 C16 116.5(2) . . ?
C14 C15 C16 119.6(2) . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Cl1 C1 1.736(2) . ?
N1 C9 1.355(3) . ?
N1 C11 1.397(3) . ?
N1 C12 1.430(3) . ?
O1 C9 1.345(3) . ?
O1 C4 1.383(3) . ?
O2 C7 1.234(3) . ?
O3 C15 1.369(3) . ?
O3 C18 1.422(3) . ?
C1 C6 1.367(3) . ?
C1 C2 1.392(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C5 C6 1.401(3) . ?
C5 C7 1.484(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.432(3) . ?
C8 C9 1.372(3) . ?
C8 C10 1.430(3) . ?
C10 C11 1.343(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 C17 1.382(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(4) . ?
C16 C17 1.373(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
_geom_hbond_publ_flag
C14 H14 Cl1 0.93 2.90 3.814(3) 167.7 3_666 yes
C13 H13 O2 0.93 2.65 3.440(3) 143.6 4_565 yes
C2 H2 O2 0.93 2.62 3.494(3) 156.7 2_656 yes
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
C6 C1 C2 C3 0.2(4) . . . . ?
Cl1 C1 C2 C3 179.62(18) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C9 O1 C4 C3 -179.98(19) . . . . ?
C9 O1 C4 C5 0.1(3) . . . . ?
C2 C3 C4 O1 -178.8(2) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
O1 C4 C5 C6 179.97(19) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
O1 C4 C5 C7 0.6(3) . . . . ?
C3 C4 C5 C7 -179.2(2) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
Cl1 C1 C6 C5 -178.37(17) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C7 C5 C6 C1 178.2(2) . . . . ?
C4 C5 C7 O2 177.2(2) . . . . ?
C6 C5 C7 O2 -2.1(3) . . . . ?
C4 C5 C7 C8 -1.6(3) . . . . ?
C6 C5 C7 C8 179.1(2) . . . . ?
O2 C7 C8 C9 -176.9(2) . . . . ?
C5 C7 C8 C9 1.8(3) . . . . ?
O2 C7 C8 C10 0.8(4) . . . . ?
C5 C7 C8 C10 179.5(3) . . . . ?
C4 O1 C9 N1 -178.68(19) . . . . ?
C4 O1 C9 C8 0.2(3) . . . . ?
C11 N1 C9 O1 179.3(2) . . . . ?
C12 N1 C9 O1 5.5(3) . . . . ?
C11 N1 C9 C8 0.2(3) . . . . ?
C12 N1 C9 C8 -173.5(2) . . . . ?
C10 C8 C9 O1 -179.6(2) . . . . ?
C7 C8 C9 O1 -1.2(4) . . . . ?
C10 C8 C9 N1 -0.6(3) . . . . ?
C7 C8 C9 N1 177.7(2) . . . . ?
C9 C8 C10 C11 0.8(3) . . . . ?
C7 C8 C10 C11 -177.1(3) . . . . ?
C8 C10 C11 N1 -0.7(3) . . . . ?
C9 N1 C11 C10 0.3(3) . . . . ?
C12 N1 C11 C10 174.0(2) . . . . ?
C9 N1 C12 C13 -47.0(3) . . . . ?
C11 N1 C12 C13 140.6(3) . . . . ?
C9 N1 C12 C17 131.3(2) . . . . ?
C11 N1 C12 C17 -41.2(3) . . . . ?
C17 C12 C13 C14 -1.4(4) . . . . ?
N1 C12 C13 C14 176.8(2) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C18 O3 C15 C14 3.4(4) . . . . ?
C18 O3 C15 C16 -176.1(2) . . . . ?
C13 C14 C15 O3 -179.0(2) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
O3 C15 C16 C17 177.8(2) . . . . ?
C14 C15 C16 C17 -1.8(4) . . . . ?
C15 C16 C17 C12 1.5(4) . . . . ?
C13 C12 C17 C16 0.1(4) . . . . ?
N1 C12 C17 C16 -178.1(2) . . . . ?
