#------------------------------------------------------------------------------
#$Date: 2022-03-21 10:50:33 +0200 (Mon, 21 Mar 2022) $
#$Revision: 273862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104814.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_8104814
loop_
_publ_author_name
'Shin, Soon Young'
'Yoo, Miri'
'Koh, Dongsoo'
_publ_section_title
;
 The crystal structure of ethyl
 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate,
 C20H21F2NO4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              307
_journal_page_last               309
_journal_paper_doi               10.1515/ncrs-2020-0566
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C20 H21 F2 N O4'
_chemical_formula_sum            'C20 H21 F2 N O4'
_chemical_formula_weight         377.38
_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                81.891(4)
_cell_angle_beta                 72.889(4)
_cell_angle_gamma                80.972(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6363(11)
_cell_length_b                   9.9144(11)
_cell_length_c                   11.8734(15)
_cell_measurement_reflns_used    7875
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.49
_cell_volume                     954.7(2)
_computing_cell_refinement       'Bruker SAINT [1]'
_computing_data_collection       'Bruker APEX2 [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'OLEX2 [4]'
_computing_publication_material  'PublCIF [5]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'PHOTON II M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28588
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.408
_diffrn_reflns_theta_min         2.090
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0466
_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)+(0.0494P)²+0.3891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3493
_reflns_number_total             4754
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0566_suppl.cif
_cod_data_source_block           A18081
_cod_database_code               8104814
_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   0.974
_shelx_estimated_absorpt_t_max   0.990
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 0.43924(18) 0.20758(16) -0.03580(14) 0.0372(3) Uani 1 1 d . . . . .
O1 O 0.54672(14) 0.16606(14) 0.01311(11) 0.0495(3) Uani 1 1 d . . . . .
C2 C 0.4766(2) 0.28001(19) -0.15938(15) 0.0471(4) Uani 1 1 d . . . . .
H2A H 0.4989 0.2117 -0.2161 0.057 Uiso 1 1 calc R U . . .
H2B H 0.5757 0.3241 -0.1745 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3383(2) 0.38891(17) -0.18094(15) 0.0435(4) Uani 1 1 d . . . . .
C4 C 0.1826(2) 0.31989(17) -0.14847(15) 0.0424(4) Uani 1 1 d . . . . .
H4A H 0.0888 0.3908 -0.1448 0.051 Uiso 1 1 calc R U . . .
H4B H 0.1884 0.2628 -0.2109 0.051 Uiso 1 1 calc R U . . .
C5 C 0.15624(18) 0.23315(15) -0.03326(13) 0.0350(3) Uani 1 1 d . . . . .
O2 O -0.00320(13) 0.20861(12) 0.01128(10) 0.0415(3) Uani 1 1 d . . . . .
C6 C -0.04388(18) 0.11542(16) 0.10913(14) 0.0374(3) Uani 1 1 d . . . . .
C7 C 0.06193(18) 0.06107(15) 0.17376(13) 0.0344(3) Uani 1 1 d . . . . .
C8 C 0.22943(17) 0.10738(15) 0.14505(13) 0.0325(3) Uani 1 1 d . . . . .
H8 H 0.3108 0.0252 0.1460 0.039 Uiso 1 1 calc R U . . .
C9 C 0.27027(17) 0.18349(15) 0.02295(13) 0.0330(3) Uani 1 1 d . . . . .
C10 C 0.3782(3) 0.4440(2) -0.31244(18) 0.0642(5) Uani 1 1 d . . . . .
H10A H 0.2900 0.5122 -0.3256 0.096 Uiso 1 1 calc R U . . .
H10B H 0.3910 0.3690 -0.3601 0.096 Uiso 1 1 calc R U . . .
H10C H 0.4788 0.4856 -0.3347 0.096 Uiso 1 1 calc R U . . .
C11 C 0.3175(3) 0.5065(2) -0.1059(2) 0.0651(6) Uani 1 1 d . . . . .
H11A H 0.2292 0.5745 -0.1192 0.098 Uiso 1 1 calc R U . . .
H11B H 0.4179 0.5484 -0.1279 0.098 Uiso 1 1 calc R U . . .
H11C H 0.2922 0.4715 -0.0229 0.098 Uiso 1 1 calc R U . . .
N1 N -0.19745(18) 0.09019(18) 0.12918(17) 0.0511(4) Uani 1 1 d . . . . .
H1A H -0.253(3) 0.128(2) 0.0792(19) 0.061(6) Uiso 1 1 d . . . . .
H1B H -0.233(3) 0.033(2) 0.1927(19) 0.057(6) Uiso 1 1 d . . . . .
C12 C 0.00812(19) -0.03686(16) 0.27452(14) 0.0385(3) Uani 1 1 d . . . . .
O3 O -0.12584(15) -0.07888(13) 0.30908(12) 0.0518(3) Uani 1 1 d . . . . .
O4 O 0.12358(14) -0.07933(12) 0.33160(10) 0.0421(3) Uani 1 1 d . . . . .
C13 C 0.0770(2) -0.17161(18) 0.43860(16) 0.0483(4) Uani 1 1 d . . . . .
H13A H 0.0549 -0.2586 0.4198 0.058 Uiso 1 1 calc R U . . .
H13B H -0.0217 -0.1305 0.4939 0.058 Uiso 1 1 calc R U . . .
C14 C 0.2171(2) -0.1955(2) 0.49238(18) 0.0618(5) Uani 1 1 d . . . . .
H14A H 0.3132 -0.2382 0.4376 0.093 Uiso 1 1 calc R U . . .
H14B H 0.1895 -0.2553 0.5656 0.093 Uiso 1 1 calc R U . . .
H14C H 0.2393 -0.1084 0.5088 0.093 Uiso 1 1 calc R U . . .
C15 C 0.23872(17) 0.19888(16) 0.23538(13) 0.0338(3) Uani 1 1 d . . . . .
C16 C 0.3450(2) 0.1610(2) 0.30491(15) 0.0462(4) Uani 1 1 d . . . . .
H16 H 0.4159 0.0786 0.2964 0.055 Uiso 1 1 calc R U . . .
C17 C 0.3447(2) 0.2468(2) 0.38686(17) 0.0566(5) Uani 1 1 d . . . . .
C18 C 0.2452(2) 0.3684(2) 0.40379(17) 0.0560(5) Uani 1 1 d . . . . .
H18 H 0.2476 0.4252 0.4602 0.067 Uiso 1 1 calc R U . . .
C19 C 0.1425(2) 0.40175(19) 0.33355(16) 0.0511(4) Uani 1 1 d . . . . .
C20 C 0.1365(2) 0.32154(17) 0.24985(15) 0.0435(4) Uani 1 1 d . . . . .
H20 H 0.0641 0.3495 0.2030 0.052 Uiso 1 1 calc R U . . .
F1 F 0.44787(18) 0.20793(19) 0.45508(14) 0.0983(5) Uani 1 1 d . . . . .
F2 F 0.03871(19) 0.52054(13) 0.34815(13) 0.0850(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'
F F 0.0171 0.0103 '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
O1 C1 C9 120.60(14) . .
O1 C1 C2 121.60(14) . .
C9 C1 C2 117.77(13) . .
C1 C2 C3 113.66(14) . .
C1 C2 H2A 108.8 . .
C3 C2 H2A 108.8 . .
C1 C2 H2B 108.8 . .
C3 C2 H2B 108.8 . .
H2A C2 H2B 107.7 . .
C11 C3 C4 111.02(15) . .
C11 C3 C2 109.79(15) . .
C4 C3 C2 107.84(14) . .
C11 C3 C10 109.58(17) . .
C4 C3 C10 108.73(15) . .
C2 C3 C10 109.85(15) . .
C5 C4 C3 112.83(13) . .
C5 C4 H4A 109.0 . .
C3 C4 H4A 109.0 . .
C5 C4 H4B 109.0 . .
C3 C4 H4B 109.0 . .
H4A C4 H4B 107.8 . .
C9 C5 O2 122.66(14) . .
C9 C5 C4 126.04(14) . .
O2 C5 C4 111.30(12) . .
C5 O2 C6 118.66(11) . .
N1 C6 C7 127.20(16) . .
N1 C6 O2 110.11(14) . .
C7 C6 O2 122.69(13) . .
C6 C7 C12 118.52(14) . .
C6 C7 C8 121.14(14) . .
C12 C7 C8 120.26(13) . .
C9 C8 C7 109.59(12) . .
C9 C8 C15 109.75(12) . .
C7 C8 C15 111.66(12) . .
C9 C8 H8 108.6 . .
C7 C8 H8 108.6 . .
C15 C8 H8 108.6 . .
C5 C9 C1 118.43(14) . .
C5 C9 C8 122.36(13) . .
C1 C9 C8 119.20(12) . .
C3 C10 H10A 109.5 . .
C3 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C3 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C3 C11 H11A 109.5 . .
C3 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C3 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C6 N1 H1A 119.2(14) . .
C6 N1 H1B 114.9(14) . .
H1A N1 H1B 126(2) . .
O3 C12 O4 121.49(15) . .
O3 C12 C7 126.45(15) . .
O4 C12 C7 112.06(13) . .
C12 O4 C13 116.05(13) . .
O4 C13 C14 106.95(15) . .
O4 C13 H13A 110.3 . .
C14 C13 H13A 110.3 . .
O4 C13 H13B 110.3 . .
C14 C13 H13B 110.3 . .
H13A C13 H13B 108.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C20 119.10(14) . .
C16 C15 C8 121.48(14) . .
C20 C15 C8 119.40(13) . .
C17 C16 C15 118.64(17) . .
C17 C16 H16 120.7 . .
C15 C16 H16 120.7 . .
F1 C17 C18 118.11(17) . .
F1 C17 C16 118.05(19) . .
C18 C17 C16 123.83(17) . .
C19 C18 C17 115.62(16) . .
C19 C18 H18 122.2 . .
C17 C18 H18 122.2 . .
F2 C19 C18 118.06(16) . .
F2 C19 C20 118.25(17) . .
C18 C19 C20 123.68(18) . .
C19 C20 C15 119.12(16) . .
C19 C20 H20 120.4 . .
C15 C20 H20 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2240(18) .
C1 C9 1.462(2) .
C1 C2 1.507(2) .
C2 C3 1.534(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C3 C11 1.523(3) .
C3 C4 1.529(2) .
C3 C10 1.535(3) .
C4 C5 1.486(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C5 C9 1.3414(19) .
C5 O2 1.3694(18) .
O2 C6 1.3732(19) .
C6 N1 1.334(2) .
C6 C7 1.362(2) .
C7 C12 1.441(2) .
C7 C8 1.515(2) .
C8 C9 1.507(2) .
C8 C15 1.5257(19) .
C8 H8 0.9900 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 H10C 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 H11C 0.9700 .
N1 H1A 0.88(2) .
N1 H1B 0.88(2) .
C12 O3 1.2264(19) .
C12 O4 1.3478(18) .
O4 C13 1.449(2) .
C13 C14 1.500(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 H14C 0.9700 .
C15 C16 1.384(2) .
C15 C20 1.386(2) .
C16 C17 1.379(2) .
C16 H16 0.9400 .
C17 F1 1.352(2) .
C17 C18 1.369(3) .
C18 C19 1.363(3) .
C18 H18 0.9400 .
C19 F2 1.362(2) .
C19 C20 1.374(2) .
C20 H20 0.9400 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O3 0.88(2) 2.00(2) 2.683(2) 133.3(19) .
N1 H1A O1 0.88(2) 2.07(2) 2.8852(19) 155.1(19) 1_455
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 C1 C2 C3 -148.01(16) . . . .
C9 C1 C2 C3 34.2(2) . . . .
C1 C2 C3 C11 66.5(2) . . . .
C1 C2 C3 C4 -54.63(19) . . . .
C1 C2 C3 C10 -172.98(15) . . . .
C11 C3 C4 C5 -73.92(18) . . . .
C2 C3 C4 C5 46.40(18) . . . .
C10 C3 C4 C5 165.46(15) . . . .
C3 C4 C5 C9 -19.1(2) . . . .
C3 C4 C5 O2 160.80(13) . . . .
C9 C5 O2 C6 -8.7(2) . . . .
C4 C5 O2 C6 171.48(13) . . . .
C5 O2 C6 N1 -171.00(13) . . . .
C5 O2 C6 C7 9.6(2) . . . .
N1 C6 C7 C12 1.2(2) . . . .
O2 C6 C7 C12 -179.53(13) . . . .
N1 C6 C7 C8 -175.59(15) . . . .
O2 C6 C7 C8 3.7(2) . . . .
C6 C7 C8 C9 -15.76(19) . . . .
C12 C7 C8 C9 167.48(13) . . . .
C6 C7 C8 C15 106.06(16) . . . .
C12 C7 C8 C15 -70.70(17) . . . .
O2 C5 C9 C1 175.85(13) . . . .
C4 C5 C9 C1 -4.3(2) . . . .
O2 C5 C9 C8 -5.7(2) . . . .
C4 C5 C9 C8 174.12(14) . . . .
O1 C1 C9 C5 178.79(14) . . . .
C2 C1 C9 C5 -3.4(2) . . . .
O1 C1 C9 C8 0.3(2) . . . .
C2 C1 C9 C8 178.08(13) . . . .
C7 C8 C9 C5 16.92(19) . . . .
C15 C8 C9 C5 -106.04(15) . . . .
C7 C8 C9 C1 -164.66(12) . . . .
C15 C8 C9 C1 72.38(16) . . . .
C6 C7 C12 O3 0.7(2) . . . .
C8 C7 C12 O3 177.50(15) . . . .
C6 C7 C12 O4 -178.49(13) . . . .
C8 C7 C12 O4 -1.65(19) . . . .
O3 C12 O4 C13 -2.9(2) . . . .
C7 C12 O4 C13 176.30(13) . . . .
C12 O4 C13 C14 -175.22(15) . . . .
C9 C8 C15 C16 -120.20(16) . . . .
C7 C8 C15 C16 118.07(16) . . . .
C9 C8 C15 C20 60.99(18) . . . .
C7 C8 C15 C20 -60.74(18) . . . .
C20 C15 C16 C17 0.3(2) . . . .
C8 C15 C16 C17 -178.48(16) . . . .
C15 C16 C17 F1 179.31(17) . . . .
C15 C16 C17 C18 -0.2(3) . . . .
F1 C17 C18 C19 -179.29(18) . . . .
C16 C17 C18 C19 0.2(3) . . . .
C17 C18 C19 F2 178.87(18) . . . .
C17 C18 C19 C20 -0.4(3) . . . .
F2 C19 C20 C15 -178.66(16) . . . .
C18 C19 C20 C15 0.6(3) . . . .
C16 C15 C20 C19 -0.5(3) . . . .
C8 C15 C20 C19 178.29(15) . . . .
