#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:50:04 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234299 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/61/4036143.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_4036143
loop_
_publ_author_name
'Martínez-López, David'
'Yu, Meng-Long'
'García-Iriepa, Cristina'
'Campos, Pedro J.'
'Frutos, Luis Manuel'
'Golen, James A.'
'Rasapalli, Sivappa'
'Sampedro, Diego'
_publ_section_title
;
 Hydantoin-based molecular photoswitches.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3929
_journal_page_last               3939
_journal_paper_doi               10.1021/acs.joc.5b00244
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.1590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8332(3)
_cell_length_b                   12.1246(4)
_cell_length_c                   13.0964(4)
_cell_measurement_reflns_used    6381
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.37
_cell_measurement_theta_min      3.45
_cell_volume                     1215.92(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus ImuSsealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7400
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         6.92
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  0.8892
_exptl_absorpt_correction_T_min  0.8248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0812P)²+0.2529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                2019
_reflns_number_total             2212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00244_si_002.cif
_cod_data_source_block           umd355_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4036143
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.27844(14) 0.64878(8) 0.40699(8) 0.0538(3) Uani 1 1 d .
O2 O 0.75156(15) 0.79036(10) 0.29904(10) 0.0642(3) Uani 1 1 d .
O3 O 0.04672(15) 0.12274(9) 0.43669(10) 0.0619(3) Uani 1 1 d .
N1 N 0.50189(16) 0.74552(10) 0.35938(9) 0.0488(3) Uani 1 1 d .
N2 N 0.66062(16) 0.61085(11) 0.31447(10) 0.0515(3) Uani 1 1 d .
C1 C 0.41376(19) 0.65072(12) 0.37549(11) 0.0452(3) Uani 1 1 d .
C2 C 0.65088(19) 0.72263(13) 0.32141(11) 0.0501(4) Uani 1 1 d .
C3 C 0.51877(18) 0.55875(12) 0.34520(10) 0.0453(3) Uani 1 1 d .
C4 C 0.49885(18) 0.44860(12) 0.34151(10) 0.0465(3) Uani 1 1 d .
H4A H 0.5876 0.4120 0.3150 0.056 Uiso 1 1 calc R
C5 C 0.37140(18) 0.37294(11) 0.36917(10) 0.0437(3) Uani 1 1 d .
C6 C 0.39392(18) 0.26105(12) 0.34690(11) 0.0484(4) Uani 1 1 d .
H6A H 0.4876 0.2405 0.3151 0.058 Uiso 1 1 calc R
C7 C 0.28426(19) 0.18053(13) 0.36980(12) 0.0505(4) Uani 1 1 d .
H7A H 0.3027 0.1056 0.3537 0.061 Uiso 1 1 calc R
C8 C 0.14653(18) 0.20849(12) 0.41642(11) 0.0480(3) Uani 1 1 d .
C9 C 0.12039(19) 0.31878(12) 0.43887(11) 0.0475(3) Uani 1 1 d .
H9A H 0.0262 0.3387 0.4705 0.057 Uiso 1 1 calc R
C10 C 0.23138(18) 0.39947(12) 0.41529(10) 0.0456(3) Uani 1 1 d .
H10A H 0.2118 0.4744 0.4308 0.055 Uiso 1 1 calc R
C11 C 0.4443(2) 0.85677(12) 0.37566(13) 0.0573(4) Uani 1 1 d .
H11A H 0.5045 0.9093 0.3385 0.086 Uiso 1 1 calc R
H11B H 0.4715 0.8738 0.4505 0.086 Uiso 1 1 calc R
H11C H 0.3180 0.8623 0.3489 0.086 Uiso 1 1 calc R
C12 C 0.8038(2) 0.55460(16) 0.28370(17) 0.0725(5) Uani 1 1 d .
H12A H 0.8945 0.6081 0.2770 0.109 Uiso 1 1 calc R
H12B H 0.7618 0.5178 0.2165 0.109 Uiso 1 1 calc R
H12C H 0.8524 0.4996 0.3367 0.109 Uiso 1 1 calc R
C13 C -0.0922(2) 0.14707(15) 0.48815(16) 0.0676(5) Uani 1 1 d .
H13A H -0.1540 0.0788 0.4979 0.101 Uiso 1 1 calc R
H13B H -0.1737 0.1987 0.4456 0.101 Uiso 1 1 calc R
H13C H -0.0445 0.1804 0.5564 0.101 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C8 O3 C13 117.48(12)
C1 N1 C2 111.92(12)
C1 N1 C11 124.77(13)
C2 N1 C11 123.26(13)
C2 N2 C3 111.63(12)
C2 N2 C12 123.22(13)
C3 N2 C12 125.10(13)
O1 C1 N1 124.61(13)
O1 C1 C3 130.25(13)
N1 C1 C3 105.13(12)
O2 C2 N2 127.41(15)
O2 C2 N1 125.98(15)
N2 C2 N1 106.61(12)
C4 C3 N2 121.86(13)
C4 C3 C1 133.43(13)
N2 C3 C1 104.69(12)
C3 C4 C5 134.20(13)
C3 C4 H4A 112.9
C5 C4 H4A 112.9
C10 C5 C6 117.13(13)
C10 C5 C4 127.19(13)
C6 C5 C4 115.68(12)
C7 C6 C5 121.90(14)
C7 C6 H6A 119.1
C5 C6 H6A 119.1
C6 C7 C8 120.10(14)
C6 C7 H7A 119.9
C8 C7 H7A 119.9
O3 C8 C7 115.53(13)
O3 C8 C9 125.18(13)
C7 C8 C9 119.29(14)
C10 C9 C8 120.21(13)
C10 C9 H9A 119.9
C8 C9 H9A 119.9
C9 C10 C5 121.36(13)
C9 C10 H10A 119.3
C5 C10 H10A 119.3
N1 C11 H11A 109.5
N1 C11 H11B 109.5
H11A C11 H11B 109.5
N1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N2 C12 H12A 109.5
N2 C12 H12B 109.5
H12A C12 H12B 109.5
N2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2160(18)
O2 C2 1.2164(18)
O3 C8 1.3601(18)
O3 C13 1.426(2)
N1 C1 1.3797(19)
N1 C2 1.3895(19)
N1 C11 1.4522(19)
N2 C2 1.362(2)
N2 C3 1.4086(18)
N2 C12 1.441(2)
C1 C3 1.488(2)
C3 C4 1.344(2)
C4 C5 1.457(2)
C4 H4A 0.9500
C5 C10 1.3965(19)
C5 C6 1.406(2)
C6 C7 1.375(2)
C6 H6A 0.9500
C7 C8 1.389(2)
C7 H7A 0.9500
C8 C9 1.394(2)
C9 C10 1.386(2)
C9 H9A 0.9500
C10 H10A 0.9500
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
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
C2 N1 C1 O1 -178.96(13)
C11 N1 C1 O1 -1.3(2)
C2 N1 C1 C3 0.40(15)
C11 N1 C1 C3 178.07(13)
C3 N2 C2 O2 -178.78(14)
C12 N2 C2 O2 3.8(3)
C3 N2 C2 N1 1.17(16)
C12 N2 C2 N1 -176.28(15)
C1 N1 C2 O2 178.98(14)
C11 N1 C2 O2 1.3(2)
C1 N1 C2 N2 -0.97(16)
C11 N1 C2 N2 -178.68(13)
C2 N2 C3 C4 177.93(13)
C12 N2 C3 C4 -4.7(2)
C2 N2 C3 C1 -0.92(15)
C12 N2 C3 C1 176.47(15)
O1 C1 C3 C4 0.9(3)
N1 C1 C3 C4 -178.36(15)
O1 C1 C3 N2 179.60(14)
N1 C1 C3 N2 0.30(14)
N2 C3 C4 C5 178.61(13)
C1 C3 C4 C5 -2.9(3)
C3 C4 C5 C10 -3.8(2)
C3 C4 C5 C6 176.47(15)
C10 C5 C6 C7 -0.4(2)
C4 C5 C6 C7 179.36(12)
C5 C6 C7 C8 -0.1(2)
C13 O3 C8 C7 177.68(14)
C13 O3 C8 C9 -2.2(2)
C6 C7 C8 O3 -179.43(13)
C6 C7 C8 C9 0.4(2)
O3 C8 C9 C10 179.57(13)
C7 C8 C9 C10 -0.3(2)
C8 C9 C10 C5 -0.2(2)
C6 C5 C10 C9 0.54(19)
C4 C5 C10 C9 -179.18(13)
