Crystal structure of ethyl 2-amino-4-(3,4-difluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C21H15F2NO5
Li, Jingwei; Nie, Xingyu; Fan, Hao; Wu, Xuejiao; Li, Xiaonan; He, Jieli; Zeitschrift für Kristallographie - New Crystal Structures 234 (2018) 77–78; doi:10.1515/ncrs-2018-0182

data_8105547
_publ_section_title
;
 Crystal structure of ethyl
 2-amino-4-(3,4-difluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]
 chromene-3-carboxylate, C21H15F2NO5
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              77
_journal_page_last               78
_journal_paper_doi               10.1515/ncrs-2018-0182
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C21 H15 F2 N O5'
_chemical_formula_sum            'C21 H15 F2 N O5'
_chemical_formula_weight         399.34
_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   geom
_cell_angle_alpha                86.51(3)
_cell_angle_beta                 84.31(3)
_cell_angle_gamma                81.06(3)
_cell_formula_units_Z            2
_cell_length_a                   5.699(3)
_cell_length_b                   9.629(4)
_cell_length_c                   16.888(2)
_cell_measurement_reflns_used    641
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.17
_cell_measurement_theta_min      2.43
_cell_volume                     910.0(6)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART (Bruker Apex-II, 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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5602
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.213
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.058(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1520
_refine_ls_R_factor_gt           0.0643
_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/[\s^2^(Fo^2^)+(0.1185P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.2270
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1708
_reflns_number_total             4062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2018-0182_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        909.9(7)
_cod_database_code               8105547
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.970
_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. Restrained distances
 C1-C2
 1.9 with sigma of 0.02
 O1-C2 = O1-C0AA
 1.4 with sigma of 0.01
 C2-C1 = C1AA-C0AA
 1.5 with sigma of 0.005
3. Rigid bond restraints
 C1, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=1-FVAR(1)
 Sof(C1)=Sof(H1C)=Sof(H1D)=Sof(H1E)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C0AA(H0AA,H0AB)
6.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C21(H21), C6(H6)
6.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
6.e Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C1AA(H1AA,H1AB,H1AC)
;