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#$Date: 2022-12-06 11:33:47 +0200 (Tue, 06 Dec 2022) $
#$Revision: 279731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106339.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_8106339
loop_
_publ_author_name
'Yang, Dao-Qiu'
'Li, Zhen-Ming'
_publ_section_title
;
 Crystal structure of ethyl
 2-amino-4-(3-cyanophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate,
 C21H22N2O4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              903
_journal_page_last               904
_journal_paper_doi               10.1515/ncrs-2018-0089
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C21 H22 N2 O4'
_chemical_formula_sum            'C21 H22 N2 O4'
_chemical_formula_weight         366.40
_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                 98.002(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1261(14)
_cell_length_b                   11.829(2)
_cell_length_c                   20.123(4)
_cell_measurement_reflns_used    2828
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.67
_cell_volume                     1915.5(6)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9508
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.594
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.065(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0394
_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)+(0.0439P)²+0.2078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2518
_reflns_number_total             3349
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0089_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1915.4(6)
_cod_database_code               8106339
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C10(H10A,H10B), C12(H12A,H12B)
2.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C20(H20)
2.e X=CH2 refined with riding coordinates:
 N2(H2C,H2D)
;
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 0.75443(13) 0.26418(9) -0.01309(5) 0.0543(3) Uani 1 1 d . . . . .
O2 O 0.88754(15) 0.09912(9) -0.01208(6) 0.0579(3) Uani 1 1 d . . . . .
O3 O 0.23526(16) 0.30296(12) 0.09097(8) 0.0881(5) Uani 1 1 d . . . . .
C1 C 0.8297(3) 0.43321(16) -0.06166(11) 0.0843(7) Uani 1 1 d . . . . .
H1A H 0.909071 0.469395 -0.085767 0.126 Uiso 1 1 calc R . . . .
H1B H 0.721478 0.436768 -0.087720 0.126 Uiso 1 1 calc R . . . .
H1C H 0.827536 0.471104 -0.019606 0.126 Uiso 1 1 calc R . . . .
C2 C 0.8771(2) 0.31435(14) -0.04926(10) 0.0652(5) Uani 1 1 d . . . . .
H2A H 0.879926 0.275123 -0.091416 0.078 Uiso 1 1 calc R . . . .
H2B H 0.986466 0.309615 -0.022992 0.078 Uiso 1 1 calc R . . . .
C3 C 0.77691(19) 0.15625(12) 0.00576(7) 0.0438(4) Uani 1 1 d . . . . .
C4 C 0.65968(18) 0.12076(11) 0.04837(7) 0.0409(4) Uani 1 1 d . . . . .
C5 C 0.66605(18) 0.01320(12) 0.07189(7) 0.0424(4) Uani 1 1 d . . . . .
C6 C 0.42640(18) 0.04048(13) 0.12405(7) 0.0444(4) Uani 1 1 d . . . . .
C7 C 0.40795(18) 0.14584(12) 0.10187(7) 0.0434(4) Uani 1 1 d . . . . .
C8 C 0.53838(17) 0.20562(11) 0.06948(7) 0.0414(4) Uani 1 1 d . . . . .
H8 H 0.484332 0.244861 0.029398 0.050 Uiso 1 1 calc R . . . .
C9 C 0.2565(2) 0.20694(16) 0.11069(9) 0.0581(5) Uani 1 1 d . . . . .
C10 C 0.1284(2) 0.14448(18) 0.14299(11) 0.0729(6) Uani 1 1 d . . . . .
H10A H 0.055843 0.104056 0.108613 0.088 Uiso 1 1 calc R . . . .
H10B H 0.061040 0.198726 0.163325 0.088 Uiso 1 1 calc R . . . .
C11 C 0.2024(2) 0.06095(17) 0.19622(9) 0.0638(5) Uani 1 1 d . . . . .
C12 C 0.3120(2) -0.01990(14) 0.16301(8) 0.0548(4) Uani 1 1 d . . . . .
H12A H 0.376492 -0.065527 0.197283 0.066 Uiso 1 1 calc R . . . .
H12B H 0.242130 -0.070383 0.133351 0.066 Uiso 1 1 calc R . . . .
C13 C 0.0639(3) -0.0056(2) 0.22196(13) 0.0993(8) Uani 1 1 d . . . . .
H13A H 0.111227 -0.058320 0.255585 0.149 Uiso 1 1 calc R . . . .
H13B H -0.008385 0.045452 0.241085 0.149 Uiso 1 1 calc R . . . .
H13C H 0.001596 -0.046049 0.185431 0.149 Uiso 1 1 calc R . . . .
C14 C 0.3033(3) 0.12266(19) 0.25455(10) 0.0823(6) Uani 1 1 d . . . . .
H14A H 0.349196 0.068774 0.287723 0.124 Uiso 1 1 calc R . . . .
H14B H 0.391773 0.163836 0.238573 0.124 Uiso 1 1 calc R . . . .
H14C H 0.232666 0.174311 0.274159 0.124 Uiso 1 1 calc R . . . .
C15 C 0.62536(17) 0.29256(11) 0.11747(7) 0.0395(3) Uani 1 1 d . . . . .
C16 C 0.70599(19) 0.26071(13) 0.17953(8) 0.0485(4) Uani 1 1 d . . . . .
H16 H 0.705556 0.184927 0.191823 0.058 Uiso 1 1 calc R . . . .
C17 C 0.7869(2) 0.33761(14) 0.22373(9) 0.0554(4) Uani 1 1 d . . . . .
H17 H 0.839144 0.313829 0.265455 0.067 Uiso 1 1 calc R . . . .
C18 C 0.7905(2) 0.44894(14) 0.20626(9) 0.0547(4) Uani 1 1 d . . . . .
H18 H 0.845773 0.501446 0.235734 0.066 Uiso 1 1 calc R . . . .
C19 C 0.7115(2) 0.48255(12) 0.14456(9) 0.0514(4) Uani 1 1 d . . . . .
C20 C 0.62807(19) 0.40522(12) 0.10054(8) 0.0473(4) Uani 1 1 d . . . . .
H20 H 0.573519 0.429479 0.059306 0.057 Uiso 1 1 calc R . . . .
C21 C 0.7155(3) 0.59931(15) 0.12602(10) 0.0695(5) Uani 1 1 d . . . . .
O4 O 0.55960(13) -0.02539(8) 0.11403(5) 0.0498(3) Uani 1 1 d . . . . .
N1 N 0.7200(3) 0.69186(14) 0.11208(11) 0.1030(7) Uani 1 1 d . . . . .
N2 N 0.77055(17) -0.06812(10) 0.06091(7) 0.0567(4) Uani 1 1 d . . . . .
H2C H 0.846454 -0.055452 0.036031 0.068 Uiso 1 1 calc R . . . .
H2D H 0.762631 -0.133695 0.078652 0.068 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'
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
C3 O1 C2 117.36(12) . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
O1 C2 C1 107.21(14) . .
O1 C2 H2A 110.3 . .
O1 C2 H2B 110.3 . .
C1 C2 H2A 110.3 . .
C1 C2 H2B 110.3 . .
H2A C2 H2B 108.5 . .
O1 C3 C4 111.98(12) . .
O2 C3 O1 121.56(13) . .
O2 C3 C4 126.46(13) . .
C3 C4 C8 119.29(12) . .
C5 C4 C3 119.23(13) . .
C5 C4 C8 121.38(13) . .
C4 C5 O4 122.10(13) . .
N2 C5 C4 128.22(14) . .
N2 C5 O4 109.66(12) . .
C7 C6 C12 125.60(14) . .
C7 C6 O4 122.64(13) . .
O4 C6 C12 111.75(13) . .
C6 C7 C8 122.49(13) . .
C6 C7 C9 118.86(14) . .
C9 C7 C8 118.63(13) . .
C4 C8 H8 108.6 . .
C4 C8 C15 111.44(12) . .
C7 C8 C4 109.77(11) . .
C7 C8 H8 108.6 . .
C7 C8 C15 109.80(11) . .
C15 C8 H8 108.6 . .
O3 C9 C7 120.70(15) . .
O3 C9 C10 122.03(15) . .
C7 C9 C10 117.24(15) . .
C9 C10 H10A 108.9 . .
C9 C10 H10B 108.9 . .
C9 C10 C11 113.34(14) . .
H10A C10 H10B 107.7 . .
C11 C10 H10A 108.9 . .
C11 C10 H10B 108.9 . .
C10 C11 C12 107.29(14) . .
C10 C11 C13 109.74(15) . .
C10 C11 C14 110.49(17) . .
C13 C11 C12 109.24(17) . .
C14 C11 C12 110.74(14) . .
C14 C11 C13 109.29(17) . .
C6 C12 C11 112.22(14) . .
C6 C12 H12A 109.2 . .
C6 C12 H12B 109.2 . .
C11 C12 H12A 109.2 . .
C11 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C8 120.79(12) . .
C20 C15 C8 121.40(13) . .
C20 C15 C16 117.81(14) . .
C15 C16 H16 119.0 . .
C17 C16 C15 121.96(14) . .
C17 C16 H16 119.0 . .
C16 C17 H17 120.1 . .
C18 C17 C16 119.84(16) . .
C18 C17 H17 120.1 . .
C17 C18 H18 120.4 . .
C17 C18 C19 119.20(15) . .
C19 C18 H18 120.4 . .
C18 C19 C20 120.84(14) . .
C18 C19 C21 119.31(16) . .
C20 C19 C21 119.84(17) . .
C15 C20 C19 120.32(15) . .
C15 C20 H20 119.8 . .
C19 C20 H20 119.8 . .
N1 C21 C19 179.1(3) . .
C5 O4 C6 118.74(11) . .
C5 N2 H2C 120.0 . .
C5 N2 H2D 120.0 . .
H2C N2 H2D 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.4417(18) .
O1 C3 1.3371(17) .
O2 C3 1.2181(17) .
O3 C9 1.207(2) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C1 C2 1.470(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.430(2) .
C4 C5 1.3560(19) .
C4 C8 1.5087(19) .
C5 O4 1.3711(17) .
C5 N2 1.3218(18) .
C6 C7 1.325(2) .
C6 C12 1.480(2) .
C6 O4 1.3711(18) .
C7 C8 1.4968(19) .
C7 C9 1.459(2) .
C8 H8 0.9800 .
C8 C15 1.516(2) .
C9 C10 1.497(2) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 C11 1.519(3) .
C11 C12 1.524(2) .
C11 C13 1.522(2) .
C11 C14 1.522(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 C16 1.379(2) .
C15 C20 1.376(2) .
C16 H16 0.9300 .
C16 C17 1.374(2) .
C17 H17 0.9300 .
C17 C18 1.364(2) .
C18 H18 0.9300 .
C18 C19 1.375(2) .
C19 C20 1.384(2) .
C19 C21 1.432(2) .
C20 H20 0.9300 .
C21 N1 1.132(2) .
N2 H2C 0.8600 .
N2 H2D 0.8600 .
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 C3 C4 C5 -179.97(13) . . . .
O1 C3 C4 C8 -3.59(19) . . . .
O2 C3 C4 C5 -0.8(2) . . . .
O2 C3 C4 C8 175.54(14) . . . .
O3 C9 C10 C11 -147.7(2) . . . .
C2 O1 C3 O2 -6.7(2) . . . .
C2 O1 C3 C4 172.50(14) . . . .
C3 O1 C2 C1 -177.58(15) . . . .
C3 C4 C5 O4 178.61(13) . . . .
C3 C4 C5 N2 0.3(2) . . . .
C3 C4 C8 C7 168.80(13) . . . .
C3 C4 C8 C15 -69.34(17) . . . .
C4 C5 O4 C6 10.7(2) . . . .
C4 C8 C15 C16 -63.20(16) . . . .
C4 C8 C15 C20 116.17(14) . . . .
C5 C4 C8 C7 -14.89(19) . . . .
C5 C4 C8 C15 106.97(15) . . . .
C6 C7 C8 C4 16.7(2) . . . .
C6 C7 C8 C15 -106.12(16) . . . .
C6 C7 C9 O3 -179.82(17) . . . .
C6 C7 C9 C10 -1.7(2) . . . .
C7 C6 C12 C11 -19.8(2) . . . .
C7 C6 O4 C5 -9.0(2) . . . .
C7 C8 C15 C16 58.64(17) . . . .
C7 C8 C15 C20 -121.99(14) . . . .
C7 C9 C10 C11 34.1(2) . . . .
C8 C4 C5 O4 2.3(2) . . . .
C8 C4 C5 N2 -176.02(15) . . . .
C8 C7 C9 O3 1.6(3) . . . .
C8 C7 C9 C10 179.75(15) . . . .
C8 C15 C16 C17 179.45(14) . . . .
C8 C15 C20 C19 -178.49(13) . . . .
C9 C7 C8 C4 -164.75(14) . . . .
C9 C7 C8 C15 72.42(17) . . . .
C9 C10 C11 C12 -56.6(2) . . . .
C9 C10 C11 C13 -175.14(18) . . . .
C9 C10 C11 C14 64.3(2) . . . .
C10 C11 C12 C6 48.67(19) . . . .
C12 C6 C7 C8 172.95(14) . . . .
C12 C6 C7 C9 -5.6(2) . . . .
C12 C6 O4 C5 172.09(12) . . . .
C13 C11 C12 C6 167.58(15) . . . .
C14 C11 C12 C6 -71.99(19) . . . .
C15 C16 C17 C18 -0.8(2) . . . .
C16 C15 C20 C19 0.9(2) . . . .
C16 C17 C18 C19 0.5(2) . . . .
C17 C18 C19 C20 0.4(2) . . . .
C17 C18 C19 C21 -179.83(16) . . . .
C18 C19 C20 C15 -1.2(2) . . . .
C20 C15 C16 C17 0.1(2) . . . .
C21 C19 C20 C15 179.12(15) . . . .
O4 C6 C7 C8 -5.7(2) . . . .
O4 C6 C7 C9 175.72(14) . . . .
O4 C6 C12 C11 159.04(13) . . . .
N2 C5 O4 C6 -170.73(13) . . . .
