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#$Date: 2023-03-10 12:12:57 +0200 (Fri, 10 Mar 2023) $
#$Revision: 281809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106917.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_8106917
loop_
_publ_author_name
'Sui, Feng'
'Li, Jing'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(2,6-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C18H16Cl2N2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              489
_journal_page_last               490
_journal_paper_doi               10.1515/ncrs-2015-0150
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C18 H16 Cl2 N2 O2'
_chemical_formula_sum            'C18 H16 Cl2 N2 O2'
_chemical_formula_weight         363.23
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                113.355(8)
_cell_angle_beta                 103.305(7)
_cell_angle_gamma                98.461(7)
_cell_formula_units_Z            2
_cell_length_a                   8.5266(7)
_cell_length_b                   11.2217(9)
_cell_length_c                   11.5785(9)
_cell_measurement_reflns_used    2287
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2340
_cell_measurement_theta_min      2.7080
_cell_volume                     953.91(16)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5968
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0878P)²+0.3604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1747
_reflns_number_gt                2639
_reflns_number_total             3355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0150_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        953.91(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106917
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.81150(12) -0.13570(8) 0.27085(9) 0.0621(3) Uani 1 1 d . . .
Cl2 Cl 0.53824(13) 0.27048(9) 0.25676(8) 0.0638(3) Uani 1 1 d . . .
C1 C 0.3597(4) 0.1179(3) 0.4144(3) 0.0421(7) Uani 1 1 d . . .
C2 C 0.4506(4) 0.0369(3) 0.3572(3) 0.0371(6) Uani 1 1 d . . .
C3 C 0.6378(3) 0.0847(3) 0.3886(3) 0.0343(6) Uani 1 1 d . . .
H3A H 0.6875 0.0241 0.4180 0.041 Uiso 1 1 calc R . .
C4 C 0.7034(3) 0.2228(3) 0.5042(2) 0.0334(6) Uani 1 1 d . . .
C5 C 0.6039(3) 0.2928(3) 0.5574(3) 0.0391(6) Uani 1 1 d . . .
C6 C 0.6577(4) 0.4270(3) 0.6740(3) 0.0526(8) Uani 1 1 d . . .
H6A H 0.6461 0.4155 0.7506 0.063 Uiso 1 1 calc R . .
H6B H 0.5839 0.4806 0.6575 0.063 Uiso 1 1 calc R . .
C7 C 0.8374(4) 0.5036(3) 0.7063(3) 0.0572(8) Uani 1 1 d . . .
C8 C 0.9461(4) 0.4048(3) 0.6957(3) 0.0528(8) Uani 1 1 d . . .
H8A H 1.0582 0.4501 0.7062 0.063 Uiso 1 1 calc R . .
H8B H 0.9533 0.3811 0.7683 0.063 Uiso 1 1 calc R . .
C9 C 0.8841(4) 0.2784(3) 0.5683(3) 0.0410(7) Uani 1 1 d . . .
C10 C 0.3634(4) -0.0967(3) 0.2610(3) 0.0447(7) Uani 1 1 d . . .
C11 C 0.6835(3) 0.0716(2) 0.2644(2) 0.0344(6) Uani 1 1 d . . .
C12 C 0.6462(4) 0.1506(3) 0.2002(3) 0.0415(7) Uani 1 1 d . . .
C13 C 0.6863(4) 0.1368(4) 0.0871(3) 0.0558(8) Uani 1 1 d . . .
H13A H 0.6600 0.1922 0.0477 0.067 Uiso 1 1 calc R . .
C14 C 0.7651(5) 0.0406(4) 0.0342(3) 0.0658(10) Uani 1 1 d . . .
H14A H 0.7938 0.0313 -0.0412 0.079 Uiso 1 1 calc R . .
C15 C 0.8022(4) -0.0426(4) 0.0915(3) 0.0587(9) Uani 1 1 d . . .
H15A H 0.8540 -0.1090 0.0547 0.070 Uiso 1 1 calc R . .
C16 C 0.7611(4) -0.0259(3) 0.2052(3) 0.0424(7) Uani 1 1 d . . .
O1 O 0.4311(3) 0.2470(2) 0.5097(2) 0.0488(5) Uani 1 1 d . . .
O2 O 0.9788(3) 0.2182(2) 0.5206(2) 0.0583(6) Uani 1 1 d . . .
N1 N 0.1940(3) 0.0871(3) 0.3881(3) 0.0648(8) Uani 1 1 d . . .
H1A H 0.1335 0.0083 0.3290 0.078 Uiso 1 1 calc R . .
H1B H 0.1478 0.1460 0.4302 0.078 Uiso 1 1 calc R . .
N2 N 0.2906(4) -0.2039(3) 0.1820(3) 0.0704(9) Uani 1 1 d . . .
C17 C 0.8967(6) 0.6176(4) 0.8495(4) 0.0948(15) Uani 1 1 d . . .
H17A H 0.8889 0.5796 0.9098 0.142 Uiso 1 1 calc R . .
H17B H 0.8275 0.6786 0.8564 0.142 Uiso 1 1 calc R . .
H17C H 1.0107 0.6653 0.8715 0.142 Uiso 1 1 calc R . .
C18 C 0.8503(6) 0.5630(4) 0.6090(5) 0.0862(13) Uani 1 1 d . . .
H18A H 0.8125 0.4917 0.5201 0.129 Uiso 1 1 calc R . .
H18B H 0.9645 0.6098 0.6303 0.129 Uiso 1 1 calc R . .
H18C H 0.7819 0.6247 0.6157 0.129 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 127.1(3) . .
N1 C1 O1 110.6(2) . .
C2 C1 O1 122.3(3) . .
C1 C2 C10 117.5(3) . .
C1 C2 C3 122.8(3) . .
C10 C2 C3 119.7(2) . .
C4 C3 C2 109.4(2) . .
C4 C3 C11 115.3(2) . .
C2 C3 C11 111.4(2) . .
C4 C3 H3A 106.7 . .
C2 C3 H3A 106.7 . .
C11 C3 H3A 106.7 . .
C5 C4 C9 118.2(3) . .
C5 C4 C3 122.7(2) . .
C9 C4 C3 118.9(2) . .
C4 C5 O1 123.3(3) . .
C4 C5 C6 126.4(3) . .
O1 C5 C6 110.3(2) . .
C5 C6 C7 113.6(2) . .
C5 C6 H6A 108.8 . .
C7 C6 H6A 108.8 . .
C5 C6 H6B 108.8 . .
C7 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
C6 C7 C8 108.0(3) . .
C6 C7 C18 110.8(3) . .
C8 C7 C18 109.6(3) . .
C6 C7 C17 108.8(3) . .
C8 C7 C17 109.6(3) . .
C18 C7 C17 110.0(3) . .
C9 C8 C7 114.6(3) . .
C9 C8 H8A 108.6 . .
C7 C8 H8A 108.6 . .
C9 C8 H8B 108.6 . .
C7 C8 H8B 108.6 . .
H8A C8 H8B 107.6 . .
O2 C9 C4 119.8(3) . .
O2 C9 C8 122.0(3) . .
C4 C9 C8 118.1(2) . .
N2 C10 C2 178.7(4) . .
C16 C11 C12 115.3(2) . .
C16 C11 C3 121.1(2) . .
C12 C11 C3 123.6(2) . .
C13 C12 C11 123.1(3) . .
C13 C12 Cl2 116.1(2) . .
C11 C12 Cl2 120.7(2) . .
C14 C13 C12 119.1(3) . .
C14 C13 H13A 120.4 . .
C12 C13 H13A 120.4 . .
C13 C14 C15 120.5(3) . .
C13 C14 H14A 119.8 . .
C15 C14 H14A 119.8 . .
C14 C15 C16 119.0(3) . .
C14 C15 H15A 120.5 . .
C16 C15 H15A 120.5 . .
C15 C16 C11 122.9(3) . .
C15 C16 Cl1 116.0(2) . .
C11 C16 Cl1 121.0(2) . .
C1 O1 C5 118.4(2) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C7 C17 H17A 109.5 . .
C7 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C7 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C7 C18 H18A 109.5 . .
C7 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C7 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
Cl1 C16 1.741(3) .
Cl2 C12 1.741(3) .
C1 N1 1.335(4) .
C1 C2 1.354(4) .
C1 O1 1.361(4) .
C2 C10 1.417(4) .
C2 C3 1.514(4) .
C3 C4 1.504(4) .
C3 C11 1.533(3) .
C3 H3A 0.9800 .
C4 C5 1.330(4) .
C4 C9 1.462(4) .
C5 O1 1.384(3) .
C5 C6 1.484(4) .
C6 C7 1.523(5) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.533(5) .
C7 C18 1.535(5) .
C7 C17 1.544(5) .
C8 C9 1.493(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O2 1.218(3) .
C10 N2 1.147(4) .
C11 C16 1.389(4) .
C11 C12 1.392(4) .
C12 C13 1.384(4) .
C13 C14 1.368(5) .
C13 H13A 0.9300 .
C14 C15 1.377(5) .
C14 H14A 0.9300 .
C15 C16 1.388(4) .
C15 H15A 0.9300 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
