Crystal structure of 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene, C22H18N2O3
Zhang, Chang-Hu; Zeitschrift für Kristallographie - New Crystal Structures 232 (2017) 565–566; doi:10.1515/ncrs-2016-0340

data_8106603
_publ_section_title
;
 Crystal structure of
 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene,
 C22H18N2O3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              565
_journal_page_last               566
_journal_paper_doi               10.1515/ncrs-2016-0340
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C22 H18 N2 O3'
_chemical_formula_sum            'C22 H18 N2 O3'
_chemical_formula_weight         358.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8532(7)
_cell_length_b                   11.3579(6)
_cell_length_c                   22.1712(18)
_cell_measurement_reflns_used    2330
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3060
_cell_measurement_theta_min      2.7960
_cell_volume                     3740.3(4)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2083
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -37.00   85.00   1.0000   44.5600
omega____ theta____ kappa____ phi______ frames
    -       17.7193    0.0000    0.0000 122

  2 omega  -25.00    2.00   1.0000   44.5600
omega____ theta____ kappa____ phi______ frames
    -      -19.2818  -99.0000  -90.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0199234000
_diffrn_orient_matrix_UB_12      0.0204932000
_diffrn_orient_matrix_UB_13      -0.0271442000
_diffrn_orient_matrix_UB_21      0.0355141000
_diffrn_orient_matrix_UB_22      0.0257930000
_diffrn_orient_matrix_UB_23      0.0168055000
_diffrn_orient_matrix_UB_31      0.0249409000
_diffrn_orient_matrix_UB_32      -0.0530203000
_diffrn_orient_matrix_UB_33      -0.0023072000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8867
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.437
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3299
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0677P)^2^+2.3236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1653
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2256
_reflns_number_total             3299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2016-0340_suppl.cif
_cod_data_source_block           a
_cod_database_code               8106603
_chemical_oxdiff_formula         CHON
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 C21B-C20 = C22A-C20 = C22B-C20 = C21A-C20
 1.5 with sigma of 0.01
 C20-H20
 0.98 with sigma of 0.01
3. Restrained planarity
 C1, C2, C3, C4, C5, O1, N1
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C20 \\sim C21B \\sim C22B \\sim C21A \\sim C22A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
5. Others
 Sof(H20A)=Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22B)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=1-FVAR(1)
 Sof(H20)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=FVAR(1)
6.a Riding coordinates:
 C20(H20)
6.b Rotating group:
 N1(H1A,H1B)
6.c Ternary CH refined with riding coordinates:
 C3(H3), C20(H20A)
6.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19)
6.e Idealised Me refined as rotating group:
 C21B(H21A,H21B,H21C), C22B(H22A,H22B,H22C), C21A(H21D,H21E,H21F), C22A(H22D,
 H22E,H22F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'