#------------------------------------------------------------------------------
#$Date: 2023-05-12 12:09:19 +0300 (Fri, 12 May 2023) $
#$Revision: 283724 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107195.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_8107195
loop_
_publ_author_name
'Liu, Tianhao'
'Lv, Menglan'
_publ_section_title
;
 Crystal structure of (Z)-3-((tert-butylamino)
 methylene)-2-(2-hydroxynaphthalen-1-yl) chroman-4-one, C24H23NO3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              707
_journal_page_last               709
_journal_paper_doi               10.1515/ncrs-2022-0097
_journal_volume                  237
_journal_year                    2022
_chemical_formula_sum            'C24 H23 N O3'
_chemical_formula_weight         373.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 99.465(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2490(11)
_cell_length_b                   15.886(2)
_cell_length_c                   16.218(2)
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.56
_cell_volume                     2096.3(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10244
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.546
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0545
_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)+(0.1008P)²+0.0443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2278
_reflns_number_total             3674
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0097_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        2096.4(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8107195
_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   0.980
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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
O1 O 0.27097(17) 0.08430(9) 0.71931(9) 0.0521(4) Uani 1 1 d . . . . .
O2 O 0.55040(19) 0.19361(9) 0.56362(9) 0.0526(4) Uani 1 1 d . . . . .
O3 O 0.95646(18) 0.13025(11) 0.68919(12) 0.0668(5) Uani 1 1 d . . . . .
H3 H 1.0559 0.1222 0.7002 0.100 Uiso 1 1 calc R U . . .
N1 N 0.4423(2) 0.17041(12) 0.84362(10) 0.0492(5) Uani 1 1 d . . . . .
H1 H 0.3619 0.1368 0.8269 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3742(2) 0.11045(13) 0.67470(12) 0.0393(5) Uani 1 1 d . . . . .
C8 C 0.5090(2) 0.16202(12) 0.70592(12) 0.0366(5) Uani 1 1 d . . . . .
C15 C 0.7641(3) 0.24002(14) 0.67316(12) 0.0422(5) Uani 1 1 d . . . . .
C5 C 0.3515(2) 0.08888(13) 0.58554(13) 0.0421(5) Uani 1 1 d . . . . .
C9 C 0.6341(2) 0.17452(13) 0.64831(12) 0.0401(5) Uani 1 1 d . . . . .
H9 H 0.6908 0.1206 0.6455 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5349(3) 0.19061(13) 0.78780(12) 0.0432(5) Uani 1 1 d . . . . .
H10 H 0.6234 0.2264 0.8044 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4370(3) 0.13416(14) 0.53279(13) 0.0455(6) Uani 1 1 d . . . . .
C24 C 0.7278(3) 0.32772(14) 0.67392(12) 0.0470(6) Uani 1 1 d . . . . .
C16 C 0.9254(3) 0.21398(15) 0.69197(13) 0.0474(6) Uani 1 1 d . . . . .
C4 C 0.2371(3) 0.02859(15) 0.55055(15) 0.0537(6) Uani 1 1 d . . . . .
H4 H 0.1792 -0.0021 0.5849 0.064 Uiso 1 1 calc R U . . .
C19 C 0.8603(3) 0.38655(16) 0.69339(13) 0.0556(7) Uani 1 1 d . . . . .
C3 C 0.2094(3) 0.01421(17) 0.46573(17) 0.0646(7) Uani 1 1 d . . . . .
H3A H 0.1349 -0.0268 0.4429 0.078 Uiso 1 1 calc R U . . .
C18 C 1.0217(3) 0.35558(18) 0.71417(15) 0.0644(7) Uani 1 1 d . . . . .
H18 H 1.1079 0.3933 0.7287 0.077 Uiso 1 1 calc R U . . .
C1 C 0.4057(3) 0.12052(17) 0.44747(14) 0.0603(7) Uani 1 1 d . . . . .
H1A H 0.4610 0.1517 0.4122 0.072 Uiso 1 1 calc R U . . .
C17 C 1.0542(3) 0.27234(17) 0.71351(15) 0.0583(7) Uani 1 1 d . . . . .
H17 H 1.1619 0.2534 0.7273 0.070 Uiso 1 1 calc R U . . .
C2 C 0.2929(3) 0.06094(18) 0.41502(16) 0.0667(7) Uani 1 1 d . . . . .
H2 H 0.2724 0.0520 0.3576 0.080 Uiso 1 1 calc R U . . .
C23 C 0.5672(3) 0.35999(17) 0.65437(15) 0.0646(7) Uani 1 1 d . . . . .
H23 H 0.4789 0.3232 0.6420 0.078 Uiso 1 1 calc R U . . .
C11 C 0.4595(4) 0.19826(18) 0.93121(16) 0.0731(8) Uani 1 1 d . . . . .
C20 C 0.8251(5) 0.47277(19) 0.69006(17) 0.0792(9) Uani 1 1 d . . . . .
H20 H 0.9112 0.5111 0.7014 0.095 Uiso 1 1 calc R U . . .
C21 C 0.6707(5) 0.50176(19) 0.6710(2) 0.0913(10) Uani 1 1 d . . . . .
H21 H 0.6508 0.5594 0.6694 0.110 Uiso 1 1 calc R U . . .
C22 C 0.5396(4) 0.4449(2) 0.6534(2) 0.0861(9) Uani 1 1 d . . . . .
H22 H 0.4326 0.4652 0.6408 0.103 Uiso 1 1 calc R U . . .
C13 C 0.6337(5) 0.1809(3) 0.9753(2) 0.1375(16) Uani 1 1 d . . . . .
H13A H 0.6536 0.1213 0.9766 0.206 Uiso 1 1 calc R U . . .
H13B H 0.6470 0.2021 1.0315 0.206 Uiso 1 1 calc R U . . .
H13C H 0.7106 0.2083 0.9457 0.206 Uiso 1 1 calc R U . . .
C14 C 0.4241(6) 0.2925(2) 0.9330(3) 0.1288(15) Uani 1 1 d . . . . .
H14A H 0.4958 0.3221 0.9020 0.193 Uiso 1 1 calc R U . . .
H14B H 0.4422 0.3119 0.9898 0.193 Uiso 1 1 calc R U . . .
H14C H 0.3119 0.3028 0.9083 0.193 Uiso 1 1 calc R U . . .
C12 C 0.3336(6) 0.1495(3) 0.9687(2) 0.158(2) Uani 1 1 d . . . . .
H12A H 0.2259 0.1617 0.9387 0.237 Uiso 1 1 calc R U . . .
H12B H 0.3392 0.1651 1.0262 0.237 Uiso 1 1 calc R U . . .
H12C H 0.3551 0.0903 0.9651 0.237 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'
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
C6 O2 C9 112.91(15) . .
C10 N1 C11 128.0(2) . .
O1 C7 C8 123.23(18) . .
O1 C7 C5 119.63(18) . .
C8 C7 C5 117.12(16) . .
C10 C8 C7 121.57(17) . .
C10 C8 C9 122.32(18) . .
C7 C8 C9 115.65(16) . .
C16 C15 C24 119.18(19) . .
C16 C15 C9 118.2(2) . .
C24 C15 C9 122.56(19) . .
C6 C5 C4 118.7(2) . .
C6 C5 C7 119.23(19) . .
C4 C5 C7 121.89(19) . .
O2 C9 C15 108.31(16) . .
O2 C9 C8 109.99(15) . .
C15 C9 C8 117.04(16) . .
N1 C10 C8 124.3(2) . .
O2 C6 C1 118.6(2) . .
O2 C6 C5 121.17(18) . .
C1 C6 C5 120.2(2) . .
C23 C24 C15 123.0(2) . .
C23 C24 C19 117.9(2) . .
C15 C24 C19 119.1(2) . .
O3 C16 C15 117.87(19) . .
O3 C16 C17 120.9(2) . .
C15 C16 C17 121.2(2) . .
C3 C4 C5 120.6(2) . .
C20 C19 C18 122.2(3) . .
C20 C19 C24 119.0(3) . .
C18 C19 C24 118.8(2) . .
C2 C3 C4 119.4(2) . .
C17 C18 C19 121.4(2) . .
C2 C1 C6 119.7(2) . .
C18 C17 C16 120.3(2) . .
C1 C2 C3 121.2(2) . .
C22 C23 C24 120.7(3) . .
N1 C11 C12 105.8(2) . .
N1 C11 C13 109.4(2) . .
C12 C11 C13 112.3(3) . .
N1 C11 C14 109.0(2) . .
C12 C11 C14 110.6(3) . .
C13 C11 C14 109.7(3) . .
C21 C20 C19 121.9(3) . .
C20 C21 C22 119.8(3) . .
C23 C22 C21 120.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.274(2) .
O2 C6 1.365(3) .
O2 C9 1.464(2) .
O3 C16 1.357(3) .
N1 C10 1.316(2) .
N1 C11 1.472(3) .
C7 C8 1.407(3) .
C7 C5 1.468(3) .
C8 C10 1.386(3) .
C8 C9 1.515(2) .
C15 C16 1.379(3) .
C15 C24 1.426(3) .
C15 C9 1.501(3) .
C5 C6 1.395(3) .
C5 C4 1.397(3) .
C6 C1 1.382(3) .
C24 C23 1.407(3) .
C24 C19 1.433(3) .
C16 C17 1.410(3) .
C4 C3 1.376(3) .
C19 C20 1.399(4) .
C19 C18 1.408(4) .
C3 C2 1.374(4) .
C18 C17 1.350(4) .
C1 C2 1.370(3) .
C23 C22 1.368(4) .
C11 C12 1.502(4) .
C11 C13 1.522(5) .
C11 C14 1.527(5) .
C20 C21 1.342(4) .
C21 C22 1.402(4) .
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
O1 C7 C8 C10 -2.5(3) . . . .
C5 C7 C8 C10 175.58(18) . . . .
O1 C7 C8 C9 169.92(18) . . . .
C5 C7 C8 C9 -12.0(3) . . . .
O1 C7 C5 C6 163.58(18) . . . .
C8 C7 C5 C6 -14.5(3) . . . .
O1 C7 C5 C4 -11.4(3) . . . .
C8 C7 C5 C4 170.45(19) . . . .
C6 O2 C9 C15 175.70(16) . . . .
C6 O2 C9 C8 -55.3(2) . . . .
C16 C15 C9 O2 -119.37(19) . . . .
C24 C15 C9 O2 57.4(2) . . . .
C16 C15 C9 C8 115.7(2) . . . .
C24 C15 C9 C8 -67.5(3) . . . .
C10 C8 C9 O2 -141.62(19) . . . .
C7 C8 C9 O2 46.1(2) . . . .
C10 C8 C9 C15 -17.5(3) . . . .
C7 C8 C9 C15 170.17(19) . . . .
C11 N1 C10 C8 -179.4(2) . . . .
C7 C8 C10 N1 2.6(3) . . . .
C9 C8 C10 N1 -169.27(19) . . . .
C9 O2 C6 C1 -150.2(2) . . . .
C9 O2 C6 C5 31.0(3) . . . .
C4 C5 C6 O2 -179.81(18) . . . .
C7 C5 C6 O2 5.0(3) . . . .
C4 C5 C6 C1 1.4(3) . . . .
C7 C5 C6 C1 -173.7(2) . . . .
C16 C15 C24 C23 179.1(2) . . . .
C9 C15 C24 C23 2.3(3) . . . .
C16 C15 C24 C19 0.6(3) . . . .
C9 C15 C24 C19 -176.14(17) . . . .
C24 C15 C16 O3 -178.77(17) . . . .
C9 C15 C16 O3 -1.8(3) . . . .
C24 C15 C16 C17 1.3(3) . . . .
C9 C15 C16 C17 178.22(18) . . . .
C6 C5 C4 C3 0.0(3) . . . .
C7 C5 C4 C3 175.0(2) . . . .
C23 C24 C19 C20 -1.6(3) . . . .
C15 C24 C19 C20 176.86(19) . . . .
C23 C24 C19 C18 179.2(2) . . . .
C15 C24 C19 C18 -2.3(3) . . . .
C5 C4 C3 C2 -1.3(4) . . . .
C20 C19 C18 C17 -177.0(2) . . . .
C24 C19 C18 C17 2.1(3) . . . .
O2 C6 C1 C2 179.7(2) . . . .
C5 C6 C1 C2 -1.5(4) . . . .
C19 C18 C17 C16 -0.2(3) . . . .
O3 C16 C17 C18 178.5(2) . . . .
C15 C16 C17 C18 -1.6(3) . . . .
C6 C1 C2 C3 0.1(4) . . . .
C4 C3 C2 C1 1.3(4) . . . .
C15 C24 C23 C22 -177.8(2) . . . .
C19 C24 C23 C22 0.6(3) . . . .
C10 N1 C11 C12 -174.1(3) . . . .
C10 N1 C11 C13 -53.0(4) . . . .
C10 N1 C11 C14 67.0(4) . . . .
C18 C19 C20 C21 -179.4(3) . . . .
C24 C19 C20 C21 1.5(4) . . . .
C19 C20 C21 C22 -0.3(4) . . . .
C24 C23 C22 C21 0.6(4) . . . .
C20 C21 C22 C23 -0.8(4) . . . .
