#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:42:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180092 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/38/7053868.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_7053868
loop_
_publ_author_name
'Jiménez-Sánchez, Arturo'
'Rodríguez, Mario'
'Métivier, Rémi'
'Ramos-Ortíz, Gabriel'
'Maldonado, Jose Luis'
'Réboles, Netzahualcoyotl'
'Farfán, Norberto'
'Nakatani, Keitaro'
'Santillan, Rosa'
_publ_section_title
;
 Synthesis and crystal structures of a series of Schiff bases: a photo-,
 solvato- and acidochromic compound
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              730
_journal_paper_doi               10.1039/c3nj00895a
_journal_volume                  38
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H20 N2 O1'
_chemical_formula_sum            'C18 H20 N2 O'
_chemical_formula_weight         280.36
_chemical_name_common            'san557 mario'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-03-04T22:28:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1828(2)
_cell_length_b                   14.6917(8)
_cell_length_c                   16.9541(5)
_cell_measurement_reflns_used    5386
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     1540.04(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.59718E-1
_diffrn_orient_matrix_UB_12      -0.500225E-1
_diffrn_orient_matrix_UB_13      -0.335514E-1
_diffrn_orient_matrix_UB_21      -0.701233E-1
_diffrn_orient_matrix_UB_22      0.275788E-1
_diffrn_orient_matrix_UB_23      -0.47475E-1
_diffrn_orient_matrix_UB_31      0.132951
_diffrn_orient_matrix_UB_32      0.370148E-1
_diffrn_orient_matrix_UB_33      -0.99697E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11063
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.0222
_exptl_absorpt_correction_T_min  0.9416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0484P)²+0.2247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2339
_reflns_number_total             3393
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3nj00895a.txt
_cod_data_source_block           san560
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7053868
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
C1 C 0.9784(4) 0.97738(16) 0.45551(13) 0.0435(5) Uani 1 1 d .
C2 C 0.7818(4) 0.94230(15) 0.48209(13) 0.0471(6) Uani 1 1 d .
H6 H 0.6916 0.9786 0.5127 0.056 Uiso 1 1 calc R
C2A C 1.1074(4) 0.91934(15) 0.41000(13) 0.0469(6) Uani 1 1 d .
H2 H 1.2395 0.9403 0.3911 0.056 Uiso 1 1 calc R
C3 C 0.7195(4) 0.85534(15) 0.46384(13) 0.0457(6) Uani 1 1 d .
H5 H 0.587 0.8344 0.4825 0.055 Uiso 1 1 calc R
C3A C 1.0434(4) 0.83207(15) 0.39252(13) 0.0439(5) Uani 1 1 d .
H3 H 1.1343 0.7954 0.3625 0.053 Uiso 1 1 calc R
C4 C 0.8463(3) 0.79681(14) 0.41841(11) 0.0375(5) Uani 1 1 d .
C5 C 0.7712(4) 0.70548(14) 0.40170(12) 0.0404(5) Uani 1 1 d .
H7 H 0.6338 0.6913 0.4203 0.049 Uiso 1 1 calc R
C6 C 0.8735(4) 0.63904(15) 0.36307(12) 0.0431(5) Uani 1 1 d .
H8 H 1.0109 0.6499 0.3428 0.052 Uiso 1 1 calc R
C7 C 0.7763(4) 0.55129(15) 0.35215(12) 0.0411(5) Uani 1 1 d .
H9 H 0.6371 0.5418 0.3712 0.049 Uiso 1 1 calc R
C8 C 0.7687(4) 0.40010(14) 0.30687(12) 0.0412(5) Uani 1 1 d .
C9 C 0.5643(3) 0.39049(14) 0.27234(12) 0.0394(5) Uani 1 1 d .
C10 C 0.4327(4) 0.46945(16) 0.24281(14) 0.0500(6) Uani 1 1 d .
H16A H 0.5283 0.513 0.2177 0.06 Uiso 1 1 calc R
H16B H 0.3317 0.4478 0.2032 0.06 Uiso 1 1 calc R
C11 C 0.4846(4) 0.30324(16) 0.26184(14) 0.0517(6) Uani 1 1 d .
H14 H 0.3488 0.2957 0.2391 0.062 Uiso 1 1 calc R
C12 C 0.5999(5) 0.22726(17) 0.28397(16) 0.0650(8) Uani 1 1 d .
H13 H 0.5422 0.1695 0.2765 0.078 Uiso 1 1 calc R
C13 C 0.8002(5) 0.23756(18) 0.31712(16) 0.0653(8) Uani 1 1 d .
H12 H 0.879 0.1866 0.3324 0.078 Uiso 1 1 calc R
C14 C 0.8851(4) 0.32331(17) 0.32790(14) 0.0551(6) Uani 1 1 d .
H11 H 1.0225 0.3297 0.3496 0.066 Uiso 1 1 calc R
C15 C 0.9043(5) 1.12471(17) 0.51736(16) 0.0644(7) Uani 1 1 d .
H18A H 0.7799 1.1394 0.486 0.097 Uiso 1 1 calc R
H18B H 0.9814 1.1795 0.53 0.097 Uiso 1 1 calc R
H18C H 0.8587 1.0954 0.5651 0.097 Uiso 1 1 calc R
C15A C 1.2442(5) 1.1000(2) 0.4463(2) 0.0862(10) Uani 1 1 d .
H17A H 1.3597 1.0607 0.4627 0.129 Uiso 1 1 calc R
H17B H 1.2662 1.1597 0.4679 0.129 Uiso 1 1 calc R
H17C H 1.2418 1.1036 0.3898 0.129 Uiso 1 1 calc R
N1 N 0.8735(3) 0.48508(13) 0.31708(11) 0.0479(5) Uani 1 1 d .
N2 N 1.0435(4) 1.06449(14) 0.47378(14) 0.0605(6) Uani 1 1 d .
O1 O 0.3153(3) 0.51412(13) 0.30376(12) 0.0624(5) Uani 1 1 d .
H1 H 0.164(6) 0.501(2) 0.298(2) 0.109(11) Uiso 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 0 '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 0.006 '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
N2 C1 C2 121.7(2)
N2 C1 C2A 121.6(2)
C2 C1 C2A 116.7(2)
C3 C2 C1 121.1(2)
C3A C2A C1 121.6(2)
C2 C3 C4 122.8(2)
C2A C3A C4 122.0(2)
C3A C4 C3 115.8(2)
C3A C4 C5 124.2(2)
C3 C4 C5 119.91(19)
C6 C5 C4 128.4(2)
C5 C6 C7 121.5(2)
N1 C7 C6 122.9(2)
C14 C8 C9 119.7(2)
C14 C8 N1 116.7(2)
C9 C8 N1 123.54(19)
C11 C9 C8 117.9(2)
C11 C9 C10 118.6(2)
C8 C9 C10 123.39(19)
O1 C10 C9 113.0(2)
C12 C11 C9 122.1(2)
C13 C12 C11 119.4(2)
C12 C13 C14 120.1(2)
C13 C14 C8 120.8(2)
C7 N1 C8 120.55(18)
C1 N2 C15A 121.4(2)
C1 N2 C15 120.8(2)
C15A N2 C15 117.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.377(3)
C1 C2 1.395(3)
C1 C2A 1.399(3)
C2 C3 1.370(3)
C2A C3A 1.374(3)
C3 C4 1.396(3)
C3A C4 1.395(3)
C4 C5 1.448(3)
C5 C6 1.335(3)
C6 C7 1.435(3)
C7 N1 1.289(3)
C8 C14 1.385(3)
C8 C9 1.400(3)
C8 N1 1.417(3)
C9 C11 1.385(3)
C9 C10 1.503(3)
C10 O1 1.423(3)
C11 C12 1.377(4)
C12 C13 1.368(4)
C13 C14 1.377(4)
C15 N2 1.439(3)
C15A N2 1.424(4)
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
O1 H1 N1 0.96(4) 1.84(4) 2.774(2) 163(3) 1_455
