#------------------------------------------------------------------------------
#$Date: 2023-01-21 11:42:27 +0200 (Sat, 21 Jan 2023) $
#$Revision: 280506 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106533.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_8106533
loop_
_publ_author_name
'Li, Jing'
'Qiu, Ya-Wen'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile
 -- ethanol (1/1), C21H26N2O6
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              351
_journal_page_last               352
_journal_paper_doi               10.1515/ncrs-2016-0257
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C21 H26 N2 O6'
_chemical_formula_weight         402.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                100.648(8)
_cell_angle_beta                 102.355(7)
_cell_angle_gamma                90.450(6)
_cell_formula_units_Z            2
_cell_length_a                   8.1553(5)
_cell_length_b                   9.0739(9)
_cell_length_c                   14.6857(14)
_cell_measurement_temperature    293(2)
_cell_volume                     1042.03(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.879
_diffrn_measured_fraction_theta_max 0.879
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.879
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7210
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         4.166
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.115(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0552
_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)+(0.0200P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3035
_reflns_number_total             4210
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0257_suppl.cif
_cod_data_source_block           a
_cod_database_code               8106533
_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.
;
loop_
_space_group_symop_operation_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_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
C1 C 0.3343(2) 0.6525(2) 0.91197(14) 0.0317(4) Uani 1 1 d . . . . .
H1 H -0.228(7) 0.716(7) 0.427(4) 0.24(3) Uiso 1 1 d . . . . .
C2 C 0.2012(2) 0.7403(2) 0.91638(13) 0.0296(4) Uani 1 1 d . . . . .
C3 C 0.0203(2) 0.6803(2) 0.88025(13) 0.0290(4) Uani 1 1 d . . . . .
H3 H -0.0422 0.7161 0.9294 0.035 Uiso 1 1 calc R U . . .
C4 C 0.0186(2) 0.5109(2) 0.86482(13) 0.0292(4) Uani 1 1 d . . . . .
C5 C 0.1562(2) 0.4340(2) 0.85899(14) 0.0320(5) Uani 1 1 d . . . . .
C6 C 0.1625(3) 0.2684(2) 0.83514(18) 0.0453(6) Uani 1 1 d . . . . .
H6A H 0.1998 0.2293 0.8929 0.054 Uiso 1 1 calc R U . . .
H6B H 0.2427 0.2421 0.7953 0.054 Uiso 1 1 calc R U . . .
C7 C -0.0073(3) 0.1989(3) 0.7841(2) 0.0576(7) Uani 1 1 d . . . . .
H7A H -0.0058 0.0908 0.7786 0.069 Uiso 1 1 calc R U . . .
H7B H -0.0337 0.2206 0.7204 0.069 Uiso 1 1 calc R U . . .
C8 C -0.1406(3) 0.2580(3) 0.83571(19) 0.0530(6) Uani 1 1 d . . . . .
H8A H -0.1279 0.2164 0.8930 0.064 Uiso 1 1 calc R U . . .
H8B H -0.2499 0.2231 0.7959 0.064 Uiso 1 1 calc R U . . .
C9 C -0.1358(3) 0.4264(2) 0.86241(15) 0.0385(5) Uani 1 1 d . . . . .
C10 C 0.2387(3) 0.8941(2) 0.95435(14) 0.0358(5) Uani 1 1 d . . . . .
C11 C -0.0653(2) 0.7334(2) 0.78898(13) 0.0294(4) Uani 1 1 d . . . . .
C12 C 0.0059(3) 0.7064(2) 0.70999(14) 0.0365(5) Uani 1 1 d . . . . .
H12 H 0.1063 0.6577 0.7126 0.044 Uiso 1 1 calc R U . . .
C13 C -0.0730(3) 0.7520(2) 0.62726(14) 0.0374(5) Uani 1 1 d . . . . .
C14 C -0.2243(3) 0.8232(2) 0.62246(14) 0.0358(5) Uani 1 1 d . . . . .
C15 C -0.2947(2) 0.8499(2) 0.70152(15) 0.0353(5) Uani 1 1 d . . . . .
C16 C -0.2151(2) 0.8060(2) 0.78500(14) 0.0327(5) Uani 1 1 d . . . . .
H16 H -0.2621 0.8251 0.8381 0.039 Uiso 1 1 calc R U . . .
C17 C 0.1404(3) 0.6634(3) 0.54474(19) 0.0620(7) Uani 1 1 d . . . . .
H17A H 0.1659 0.6557 0.4832 0.093 Uiso 1 1 calc R U . . .
H17B H 0.2274 0.7235 0.5917 0.093 Uiso 1 1 calc R U . . .
H17C H 0.1333 0.5649 0.5592 0.093 Uiso 1 1 calc R U . . .
C18 C -0.2663(4) 1.0064(3) 0.5263(2) 0.0682(8) Uani 1 1 d . . . . .
H18A H -0.3287 1.0233 0.4661 0.102 Uiso 1 1 calc R U . . .
H18B H -0.2943 1.0789 0.5764 0.102 Uiso 1 1 calc R U . . .
H18C H -0.1482 1.0164 0.5286 0.102 Uiso 1 1 calc R U . . .
C19 C -0.5290(3) 0.9420(3) 0.76493(19) 0.0609(7) Uani 1 1 d . . . . .
H19A H -0.6301 0.9932 0.7474 0.091 Uiso 1 1 calc R U . . .
H19B H -0.5569 0.8459 0.7776 0.091 Uiso 1 1 calc R U . . .
H19C H -0.4581 1.0007 0.8208 0.091 Uiso 1 1 calc R U . . .
C20 C -0.4476(4) 0.6522(5) 0.3273(2) 0.0992(13) Uani 1 1 d . . . . .
H20A H -0.4789 0.6171 0.2591 0.119 Uiso 1 1 calc R U . . .
H20B H -0.4823 0.7546 0.3403 0.119 Uiso 1 1 calc R U . . .
C21 C -0.5397(6) 0.5607(5) 0.3718(3) 0.1276(17) Uani 1 1 d . . . . .
H21A H -0.6581 0.5669 0.3479 0.191 Uiso 1 1 calc R U . . .
H21B H -0.5094 0.4583 0.3578 0.191 Uiso 1 1 calc R U . . .
H21C H -0.5128 0.5961 0.4393 0.191 Uiso 1 1 calc R U . . .
O1 O 0.31334(16) 0.50187(15) 0.87625(11) 0.0395(4) Uani 1 1 d . . . . .
O2 O -0.2563(2) 0.4905(2) 0.88539(13) 0.0599(5) Uani 1 1 d . . . . .
O3 O -0.0158(2) 0.7317(2) 0.54489(11) 0.0560(5) Uani 1 1 d . . . . .
O4 O -0.3075(2) 0.85956(18) 0.53771(10) 0.0487(4) Uani 1 1 d . . . . .
O5 O -0.44315(19) 0.9216(2) 0.68965(12) 0.0542(5) Uani 1 1 d . . . . .
O O -0.2741(3) 0.6537(3) 0.35547(17) 0.0962(8) Uani 1 1 d . . . . .
N1 N 0.4973(2) 0.6928(2) 0.93892(14) 0.0465(5) Uani 1 1 d . . . . .
H1A H 0.5289 0.7851 0.9626 0.056 Uiso 1 1 calc R U . . .
H1B H 0.5709 0.6266 0.9326 0.056 Uiso 1 1 calc R U . . .
N2 N 0.2743(3) 1.0182(2) 0.98594(15) 0.0560(6) 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 128.33(19) . .
N1 C1 O1 109.97(17) . .
C2 C1 O1 121.69(17) . .
C1 C2 C10 116.48(18) . .
C1 C2 C3 122.95(17) . .
C10 C2 C3 120.54(17) . .
C4 C3 C2 108.14(15) . .
C4 C3 C11 111.06(15) . .
C2 C3 C11 112.49(15) . .
C4 C3 H3 108.3 . .
C2 C3 H3 108.3 . .
C11 C3 H3 108.3 . .
C5 C4 C9 117.66(18) . .
C5 C4 C3 122.71(18) . .
C9 C4 C3 119.50(17) . .
C4 C5 O1 122.86(18) . .
C4 C5 C6 126.08(19) . .
O1 C5 C6 111.05(17) . .
C5 C6 C7 110.49(19) . .
C5 C6 H6A 109.6 . .
C7 C6 H6A 109.6 . .
C5 C6 H6B 109.6 . .
C7 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
C6 C7 C8 111.1(2) . .
C6 C7 H7A 109.4 . .
C8 C7 H7A 109.4 . .
C6 C7 H7B 109.4 . .
C8 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
C7 C8 C9 114.00(19) . .
C7 C8 H8A 108.8 . .
C9 C8 H8A 108.8 . .
C7 C8 H8B 108.8 . .
C9 C8 H8B 108.8 . .
H8A C8 H8B 107.6 . .
O2 C9 C4 120.8(2) . .
O2 C9 C8 120.6(2) . .
C4 C9 C8 118.55(19) . .
N2 C10 C2 177.9(2) . .
C16 C11 C12 120.09(18) . .
C16 C11 C3 120.01(17) . .
C12 C11 C3 119.89(17) . .
C13 C12 C11 119.80(19) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
O3 C13 C12 125.33(19) . .
O3 C13 C14 114.28(18) . .
C12 C13 C14 120.38(19) . .
O4 C14 C15 120.46(19) . .
O4 C14 C13 119.89(19) . .
C15 C14 C13 119.57(18) . .
O5 C15 C14 115.01(18) . .
O5 C15 C16 124.69(19) . .
C14 C15 C16 120.29(19) . .
C11 C16 C15 119.86(19) . .
C11 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
O3 C17 H17A 109.5 . .
O3 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
O3 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O4 C18 H18A 109.5 . .
O4 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O4 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O5 C19 H19A 109.5 . .
O5 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O5 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O C20 C21 115.6(3) . .
O C20 H20A 108.4 . .
C21 C20 H20A 108.4 . .
O C20 H20B 108.4 . .
C21 C20 H20B 108.4 . .
H20A C20 H20B 107.5 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C1 O1 C5 118.82(15) . .
C13 O3 C17 117.76(17) . .
C14 O4 C18 114.34(18) . .
C15 O5 C19 118.06(17) . .
C20 O H1 112(3) . .
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 1.331(2) .
C1 C2 1.357(3) .
C1 O1 1.366(2) .
C2 C10 1.409(3) .
C2 C3 1.517(3) .
C3 C4 1.510(3) .
C3 C11 1.536(2) .
C3 H3 0.9800 .
C4 C5 1.336(3) .
C4 C9 1.460(3) .
C5 O1 1.370(2) .
C5 C6 1.483(3) .
C6 C7 1.498(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.502(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.504(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O2 1.223(3) .
C10 N2 1.145(3) .
C11 C16 1.388(3) .
C11 C12 1.389(3) .
C12 C13 1.385(3) .
C12 H12 0.9300 .
C13 O3 1.369(2) .
C13 C14 1.391(3) .
C14 O4 1.383(2) .
C14 C15 1.386(3) .
C15 O5 1.372(2) .
C15 C16 1.388(3) .
C16 H16 0.9300 .
C17 O3 1.421(3) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 O4 1.420(3) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 O5 1.416(3) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 O 1.385(4) .
C20 C21 1.443(5) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
O H1 1.09(6) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
