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#$Date: 2023-03-24 10:05:06 +0200 (Fri, 24 Mar 2023) $
#$Revision: 282034 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106972.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_8106972
loop_
_publ_author_name
'Li, Jing'
'Sui, Feng'
_publ_section_title
;
 Crystal structure of
 2-amino-7,7-dimethyl-5-oxo-4-(3-phenoxy-phenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              673
_journal_page_last               675
_journal_paper_doi               10.1515/ncrs-2015-0082
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C24 H22 N2 O3'
_chemical_formula_sum            'C24 H22 N2 O3'
_chemical_formula_weight         386.44
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.293(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.130(8)
_cell_length_b                   8.825(2)
_cell_length_c                   16.021(4)
_cell_measurement_reflns_used    4653
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5750
_cell_measurement_theta_min      2.6622
_cell_volume                     4145.8(18)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16480
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.6000
_exptl_crystal_size_mid          0.5000
_exptl_crystal_size_min          0.3000
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0713P)²+1.8247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                3282
_reflns_number_total             3629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0082_suppl.cif
_cod_data_source_block           a
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8106972
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.04952(4) 0.65509(16) 0.03549(8) 0.0397(3) Uani 1 1 d . . .
C2 C 0.03860(4) 0.69364(16) -0.04881(8) 0.0403(3) Uani 1 1 d . . .
C3 C 0.05318(4) 0.60121(16) -0.11803(8) 0.0403(3) Uani 1 1 d . . .
H3A H 0.0262 0.5836 -0.1646 0.048 Uiso 1 1 calc R . .
C4 C 0.07048(4) 0.45051(15) -0.08095(8) 0.0404(3) Uani 1 1 d . . .
C5 C 0.07960(4) 0.42028(15) 0.00310(8) 0.0397(3) Uani 1 1 d . . .
C6 C 0.01555(5) 0.83149(18) -0.07267(8) 0.0457(3) Uani 1 1 d . . .
C7 C 0.09899(6) 0.27736(17) 0.04479(10) 0.0511(4) Uani 1 1 d . . .
H7A H 0.0746 0.2170 0.0579 0.061 Uiso 1 1 calc R . .
H7B H 0.1202 0.3014 0.0985 0.061 Uiso 1 1 calc R . .
C8 C 0.12384(6) 0.18327(18) -0.01072(11) 0.0596(4) Uani 1 1 d . . .
C9 C 0.09408(8) 0.17907(19) -0.10193(11) 0.0703(5) Uani 1 1 d . . .
H9A H 0.1113 0.1311 -0.1390 0.084 Uiso 1 1 calc R . .
H9B H 0.0677 0.1159 -0.1021 0.084 Uiso 1 1 calc R . .
C10 C 0.07777(5) 0.32993(18) -0.13923(9) 0.0523(4) Uani 1 1 d . . .
C11 C 0.13104(9) 0.0224(2) 0.02596(14) 0.0886(7) Uani 1 1 d . . .
H11A H 0.1500 0.0262 0.0830 0.133 Uiso 1 1 calc R . .
H11B H 0.1456 -0.0384 -0.0097 0.133 Uiso 1 1 calc R . .
H11C H 0.1021 -0.0214 0.0275 0.133 Uiso 1 1 calc R . .
C12 C 0.17032(7) 0.2536(2) -0.01059(14) 0.0781(6) Uani 1 1 d . . .
H12A H 0.1887 0.2553 0.0469 0.117 Uiso 1 1 calc R . .
H12B H 0.1661 0.3552 -0.0324 0.117 Uiso 1 1 calc R . .
H12C H 0.1853 0.1943 -0.0462 0.117 Uiso 1 1 calc R . .
C13 C 0.08836(4) 0.68770(15) -0.15476(8) 0.0393(3) Uani 1 1 d . . .
C14 C 0.13453(5) 0.66831(18) -0.12111(9) 0.0497(4) Uani 1 1 d . . .
H14A H 0.1444 0.5999 -0.0766 0.060 Uiso 1 1 calc R . .
C15 C 0.16602(5) 0.7498(2) -0.15310(10) 0.0596(4) Uani 1 1 d . . .
C16 C 0.15218(6) 0.8555(2) -0.21741(10) 0.0592(4) Uani 1 1 d . . .
H16A H 0.1735 0.9117 -0.2381 0.071 Uiso 1 1 calc R . .
C17 C 0.10628(6) 0.87563(18) -0.25019(10) 0.0540(4) Uani 1 1 d . . .
H17A H 0.0965 0.9469 -0.2932 0.065 Uiso 1 1 calc R . .
C18 C 0.07442(5) 0.79187(18) -0.22034(9) 0.0480(4) Uani 1 1 d . . .
H18A H 0.0435 0.8054 -0.2443 0.058 Uiso 1 1 calc R . .
C19 C 0.24566(5) 0.7516(2) -0.15414(12) 0.0648(5) Uani 1 1 d . . .
C20 C 0.28206(6) 0.8282(3) -0.10870(13) 0.0759(6) Uani 1 1 d . . .
H20A H 0.2824 0.8648 -0.0541 0.091 Uiso 1 1 calc R . .
C21 C 0.31871(7) 0.8507(3) -0.1453(2) 0.1019(8) Uani 1 1 d . . .
H21A H 0.3443 0.9018 -0.1146 0.122 Uiso 1 1 calc R . .
C22 C 0.31808(9) 0.7999(4) -0.2251(2) 0.1137(10) Uani 1 1 d . . .
H22A H 0.3428 0.8171 -0.2495 0.136 Uiso 1 1 calc R . .
C23 C 0.28096(11) 0.7232(4) -0.26949(19) 0.1148(9) Uani 1 1 d . . .
H23A H 0.2804 0.6877 -0.3244 0.138 Uiso 1 1 calc R . .
C24 C 0.24443(9) 0.6980(3) -0.23424(16) 0.0967(7) Uani 1 1 d . . .
H24A H 0.2191 0.6450 -0.2645 0.116 Uiso 1 1 calc R . .
O1 O 0.07144(3) 0.52214(11) 0.06310(5) 0.0434(3) Uani 1 1 d . . .
O2 O 0.06920(5) 0.35256(15) -0.21663(7) 0.0714(4) Uani 1 1 d . . .
O3 O 0.21102(4) 0.7228(2) -0.11291(9) 0.1097(7) Uani 1 1 d . . .
N1 N 0.04134(5) 0.73343(16) 0.10149(7) 0.0545(3) Uani 1 1 d . . .
H1A H 0.0276 0.8194 0.0929 0.065 Uiso 1 1 calc R . .
H1B H 0.0498 0.6980 0.1527 0.065 Uiso 1 1 calc R . .
N2 N -0.00354(5) 0.94265(18) -0.09400(8) 0.0619(4) Uani 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'
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 127.76(13) . .
N1 C1 O1 110.58(11) . .
C2 C1 O1 121.66(12) . .
C1 C2 C6 118.54(12) . .
C1 C2 C3 123.12(13) . .
C6 C2 C3 118.17(11) . .
C4 C3 C2 108.60(10) . .
C4 C3 C13 112.72(11) . .
C2 C3 C13 110.79(11) . .
C4 C3 H3A 108.2 . .
C2 C3 H3A 108.2 . .
C13 C3 H3A 108.2 . .
C5 C4 C10 118.06(13) . .
C5 C4 C3 123.20(12) . .
C10 C4 C3 118.74(12) . .
C4 C5 O1 122.92(13) . .
C4 C5 C7 126.26(13) . .
O1 C5 C7 110.82(11) . .
N2 C6 C2 178.44(15) . .
C5 C7 C8 113.21(12) . .
C5 C7 H7A 108.9 . .
C8 C7 H7A 108.9 . .
C5 C7 H7B 108.9 . .
C8 C7 H7B 108.9 . .
H7A C7 H7B 107.7 . .
C9 C8 C12 110.26(15) . .
C9 C8 C7 108.08(15) . .
C12 C8 C7 110.40(14) . .
C9 C8 C11 110.13(15) . .
C12 C8 C11 109.03(17) . .
C7 C8 C11 108.93(14) . .
C10 C9 C8 115.28(13) . .
C10 C9 H9A 108.5 . .
C8 C9 H9A 108.5 . .
C10 C9 H9B 108.5 . .
C8 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
O2 C10 C4 119.98(15) . .
O2 C10 C9 121.58(14) . .
C4 C10 C9 118.40(13) . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C12 H12A 109.5 . .
C8 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C8 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C18 118.69(12) . .
C14 C13 C3 120.84(12) . .
C18 C13 C3 120.42(12) . .
C15 C14 C13 120.48(14) . .
C15 C14 H14A 119.8 . .
C13 C14 H14A 119.8 . .
C14 C15 O3 115.00(15) . .
C14 C15 C16 120.90(15) . .
O3 C15 C16 124.01(14) . .
C17 C16 C15 118.52(14) . .
C17 C16 H16A 120.7 . .
C15 C16 H16A 120.7 . .
C16 C17 C18 121.14(14) . .
C16 C17 H17A 119.4 . .
C18 C17 H17A 119.4 . .
C17 C18 C13 120.24(14) . .
C17 C18 H18A 119.9 . .
C13 C18 H18A 119.9 . .
C20 C19 C24 121.70(18) . .
C20 C19 O3 116.34(18) . .
C24 C19 O3 121.85(18) . .
C19 C20 C21 118.3(2) . .
C19 C20 H20A 120.9 . .
C21 C20 H20A 120.9 . .
C22 C21 C20 121.1(2) . .
C22 C21 H21A 119.4 . .
C20 C21 H21A 119.4 . .
C21 C22 C23 119.4(2) . .
C21 C22 H22A 120.3 . .
C23 C22 H22A 120.3 . .
C22 C23 C24 120.6(3) . .
C22 C23 H23A 119.7 . .
C24 C23 H23A 119.7 . .
C19 C24 C23 118.9(2) . .
C19 C24 H24A 120.5 . .
C23 C24 H24A 120.5 . .
C1 O1 C5 118.91(10) . .
C19 O3 C15 120.95(14) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.3330(17) .
C1 C2 1.3578(18) .
C1 O1 1.3690(17) .
C2 C6 1.409(2) .
C2 C3 1.5207(18) .
C3 C4 1.500(2) .
C3 C13 1.5294(18) .
C3 H3A 0.9800 .
C4 C5 1.3379(18) .
C4 C10 1.465(2) .
C5 O1 1.3788(16) .
C5 C7 1.483(2) .
C6 N2 1.149(2) .
C7 C8 1.532(2) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.529(3) .
C8 C12 1.531(3) .
C8 C11 1.533(2) .
C9 C10 1.495(2) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 O2 1.2235(19) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 C14 1.382(2) .
C13 C18 1.387(2) .
C14 C15 1.380(2) .
C14 H14A 0.9300 .
C15 O3 1.381(2) .
C15 C16 1.381(2) .
C16 C17 1.374(2) .
C16 H16A 0.9300 .
C17 C18 1.381(2) .
C17 H17A 0.9300 .
C18 H18A 0.9300 .
C19 C20 1.350(3) .
C19 C24 1.360(3) .
C19 O3 1.381(2) .
C20 C21 1.379(3) .
C20 H20A 0.9300 .
C21 C22 1.350(4) .
C21 H21A 0.9300 .
C22 C23 1.359(4) .
C22 H22A 0.9300 .
C23 C24 1.366(4) .
C23 H23A 0.9300 .
C24 H24A 0.9300 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
