#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/54/7105407.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_7105407
loop_
_publ_author_name
'Harada, Jun'
'Kawazoe, Yuta'
'Ogawa, Keiichiro'
_publ_section_title
;
 Photochromism of spiropyrans and spirooxazines in the solid state: low
 temperature enhances photocoloration
;
_journal_issue                   15
_journal_name_full               'Chemical Communications'
_journal_page_first              2593
_journal_paper_doi               10.1039/b925514a
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C23 H21 N O'
_chemical_formula_weight         327.41
_chemical_melting_point          451.4
_chemical_name_systematic
;
1,3,3-Trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b]pyran]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.501(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6137(12)
_cell_length_b                   6.3473(5)
_cell_length_c                   19.4928(16)
_cell_measurement_reflns_used    4378
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      2.9
_cell_volume                     1758.1(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26272
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            pale_pink
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0706P)²+0.3652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1588
_reflns_number_gt                2984
_reflns_number_total             5123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b925514a.txt
_cod_data_source_block           SNP_rt
_cod_original_sg_symbol_H-M      P_1_21/n_1
_cod_database_code               7105407
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55334(10) 0.3057(2) 0.13611(8) 0.0376(3) Uani 1 1 d . . .
C2 C 0.58456(12) 0.4711(3) 0.09940(10) 0.0495(4) Uani 1 1 d . . .
C3 C 0.67438(13) 0.4701(3) 0.09137(10) 0.0525(5) Uani 1 1 d . . .
C4 C 0.73766(11) 0.3059(3) 0.11867(8) 0.0430(4) Uani 1 1 d . . .
C5 C 0.83067(13) 0.3006(3) 0.10890(10) 0.0536(5) Uani 1 1 d . . .
C6 C 0.88985(13) 0.1411(4) 0.13525(10) 0.0596(5) Uani 1 1 d . . .
C7 C 0.85944(13) -0.0223(4) 0.17300(11) 0.0610(5) Uani 1 1 d . . .
C8 C 0.77038(12) -0.0224(3) 0.18322(10) 0.0505(4) Uani 1 1 d . . .
C9 C 0.70633(10) 0.1402(3) 0.15658(8) 0.0381(3) Uani 1 1 d . . .
C10 C 0.61214(10) 0.1441(2) 0.16561(8) 0.0366(3) Uani 1 1 d . . .
C11 C 0.57465(12) -0.0076(3) 0.20781(9) 0.0447(4) Uani 1 1 d . . .
C12 C 0.48497(11) -0.0056(3) 0.20966(9) 0.0459(4) Uani 1 1 d . . .
C13 C 0.41472(10) 0.1376(2) 0.16437(8) 0.0383(4) Uani 1 1 d . . .
C14 C 0.26394(10) 0.2672(2) 0.15149(8) 0.0390(4) Uani 1 1 d . . .
C15 C 0.18833(12) 0.3874(3) 0.16037(11) 0.0502(4) Uani 1 1 d . . .
C16 C 0.11107(14) 0.4007(4) 0.10410(13) 0.0638(5) Uani 1 1 d . . .
C17 C 0.10834(15) 0.2984(4) 0.04182(13) 0.0727(6) Uani 1 1 d . . .
C18 C 0.18477(14) 0.1764(4) 0.03333(11) 0.0621(5) Uani 1 1 d . . .
C19 C 0.26227(11) 0.1618(3) 0.08891(9) 0.0423(4) Uani 1 1 d . . .
C20 C 0.35092(11) 0.0320(3) 0.09746(9) 0.0420(4) Uani 1 1 d . . .
C21 C 0.38037(15) 0.3611(4) 0.26108(11) 0.0538(5) Uani 1 1 d . . .
C22 C 0.32706(16) -0.1965(3) 0.11319(13) 0.0594(5) Uani 1 1 d . . .
C23 C 0.39561(17) 0.0340(4) 0.03434(11) 0.0591(5) Uani 1 1 d . . .
N1 N 0.34744(9) 0.2231(2) 0.20117(7) 0.0406(3) Uani 1 1 d . . .
O1 O 0.46233(7) 0.31962(17) 0.14223(6) 0.0443(3) Uani 1 1 d . . .
H2 H 0.5417(14) 0.585(3) 0.0827(10) 0.062(6) Uiso 1 1 d . . .
H3 H 0.6965(15) 0.583(4) 0.0661(12) 0.075(6) Uiso 1 1 d . . .
H5 H 0.8488(14) 0.415(3) 0.0818(11) 0.066(6) Uiso 1 1 d . . .
H6 H 0.9536(15) 0.135(3) 0.1289(10) 0.065(6) Uiso 1 1 d . . .
H7 H 0.9034(15) -0.140(3) 0.1909(11) 0.071(6) Uiso 1 1 d . . .
H8 H 0.7503(13) -0.140(3) 0.2092(10) 0.058(5) Uiso 1 1 d . . .
H11 H 0.6158(12) -0.104(3) 0.2352(9) 0.050(5) Uiso 1 1 d . . .
H12 H 0.4614(12) -0.103(3) 0.2415(10) 0.054(5) Uiso 1 1 d . . .
H15 H 0.1888(13) 0.470(3) 0.2065(10) 0.057(5) Uiso 1 1 d . . .
H16 H 0.0552(16) 0.492(4) 0.1107(11) 0.079(7) Uiso 1 1 d . . .
H17 H 0.0556(18) 0.290(4) 0.0047(14) 0.096(8) Uiso 1 1 d . . .
H18 H 0.1850(12) 0.099(3) -0.0104(10) 0.050(5) Uiso 1 1 d . . .
H211 H 0.4023(17) 0.494(4) 0.2443(13) 0.093(8) Uiso 1 1 d . . .
H212 H 0.3305(16) 0.378(4) 0.2873(12) 0.083(7) Uiso 1 1 d . . .
H213 H 0.4356(18) 0.291(4) 0.2942(13) 0.089(8) Uiso 1 1 d . . .
H221 H 0.3014(14) -0.207(3) 0.1567(11) 0.067(6) Uiso 1 1 d . . .
H222 H 0.2736(14) -0.263(3) 0.0677(11) 0.065(6) Uiso 1 1 d . . .
H223 H 0.3825(15) -0.287(3) 0.1205(10) 0.064(6) Uiso 1 1 d . . .
H231 H 0.4576(16) -0.050(4) 0.0464(12) 0.079(7) Uiso 1 1 d . . .
H232 H 0.4085(15) 0.183(4) 0.0200(12) 0.075(7) Uiso 1 1 d . . .
H233 H 0.3536(16) -0.038(4) -0.0040(13) 0.085(8) 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 0.0000 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'
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
_geom_angle_publ_flag
O1 C1 C10 122.56(13) . . ?
O1 C1 C2 115.76(14) . . ?
C10 C1 C2 121.65(14) . . ?
C3 C2 C1 119.53(17) . . ?
C3 C2 H2 122.3(12) . . ?
C1 C2 H2 118.1(12) . . ?
C2 C3 C4 121.70(16) . . ?
C2 C3 H3 120.1(13) . . ?
C4 C3 H3 118.2(13) . . ?
C3 C4 C5 122.10(16) . . ?
C3 C4 C9 118.69(14) . . ?
C5 C4 C9 119.21(17) . . ?
C6 C5 C4 121.03(19) . . ?
C6 C5 H5 122.3(12) . . ?
C4 C5 H5 116.6(12) . . ?
C5 C6 C7 119.99(17) . . ?
C5 C6 H6 122.1(13) . . ?
C7 C6 H6 117.9(12) . . ?
C8 C7 C6 120.52(19) . . ?
C8 C7 H7 120.6(12) . . ?
C6 C7 H7 118.8(12) . . ?
C7 C8 C9 121.41(19) . . ?
C7 C8 H8 119.1(11) . . ?
C9 C8 H8 119.5(11) . . ?
C8 C9 C4 117.84(15) . . ?
C8 C9 C10 122.95(15) . . ?
C4 C9 C10 119.21(14) . . ?
C1 C10 C9 119.19(14) . . ?
C1 C10 C11 116.69(13) . . ?
C9 C10 C11 124.03(14) . . ?
C12 C11 C10 121.14(15) . . ?
C12 C11 H11 120.1(11) . . ?
C10 C11 H11 118.7(11) . . ?
C11 C12 C13 122.60(14) . . ?
C11 C12 H12 120.2(11) . . ?
C13 C12 H12 117.2(11) . . ?
N1 C13 O1 105.90(12) . . ?
N1 C13 C12 112.73(13) . . ?
O1 C13 C12 110.22(12) . . ?
N1 C13 C20 103.38(12) . . ?
O1 C13 C20 108.89(12) . . ?
C12 C13 C20 115.13(14) . . ?
C15 C14 C19 121.64(16) . . ?
C15 C14 N1 128.04(16) . . ?
C19 C14 N1 110.24(13) . . ?
C16 C15 C14 117.52(18) . . ?
C16 C15 H15 119.7(11) . . ?
C14 C15 H15 122.7(11) . . ?
C17 C16 C15 121.64(19) . . ?
C17 C16 H16 121.1(12) . . ?
C15 C16 H16 117.3(12) . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 H17 124.4(16) . . ?
C18 C17 H17 114.7(16) . . ?
C19 C18 C17 118.5(2) . . ?
C19 C18 H18 118.7(11) . . ?
C17 C18 H18 122.8(11) . . ?
C18 C19 C14 120.17(16) . . ?
C18 C19 C20 130.59(17) . . ?
C14 C19 C20 109.12(14) . . ?
C19 C20 C23 115.15(15) . . ?
C19 C20 C22 107.90(14) . . ?
C23 C20 C22 109.18(16) . . ?
C19 C20 C13 100.78(12) . . ?
C23 C20 C13 112.67(15) . . ?
C22 C20 C13 110.86(15) . . ?
N1 C21 H211 108.8(15) . . ?
N1 C21 H212 109.7(14) . . ?
H211 C21 H212 114(2) . . ?
N1 C21 H213 108.4(14) . . ?
H211 C21 H213 108(2) . . ?
H212 C21 H213 107.1(19) . . ?
C20 C22 H221 112.1(12) . . ?
C20 C22 H222 110.4(11) . . ?
H221 C22 H222 108.3(15) . . ?
C20 C22 H223 111.4(12) . . ?
H221 C22 H223 107.3(17) . . ?
H222 C22 H223 107.1(16) . . ?
C20 C23 H231 109.4(13) . . ?
C20 C23 H232 111.8(12) . . ?
H231 C23 H232 109.5(17) . . ?
C20 C23 H233 107.8(14) . . ?
H231 C23 H233 107.4(19) . . ?
H232 C23 H233 110.8(19) . . ?
C14 N1 C21 120.60(15) . . ?
C14 N1 C13 108.37(12) . . ?
C21 N1 C13 119.25(13) . . ?
C1 O1 C13 120.92(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3657(17) . ?
C1 C10 1.375(2) . ?
C1 C2 1.405(2) . ?
C2 C3 1.358(2) . ?
C2 H2 0.96(2) . ?
C3 C4 1.412(2) . ?
C3 H3 0.97(2) . ?
C4 C5 1.416(2) . ?
C4 C9 1.421(2) . ?
C5 C6 1.352(3) . ?
C5 H5 0.97(2) . ?
C6 C7 1.403(3) . ?
C6 H6 0.97(2) . ?
C7 C8 1.362(2) . ?
C7 H7 0.99(2) . ?
C8 C9 1.408(2) . ?
C8 H8 0.98(2) . ?
C9 C10 1.428(2) . ?
C10 C11 1.454(2) . ?
C11 C12 1.320(2) . ?
C11 H11 0.932(19) . ?
C12 C13 1.495(2) . ?
C12 H12 0.992(19) . ?
C13 N1 1.4510(19) . ?
C13 O1 1.4646(18) . ?
C13 C20 1.566(2) . ?
C14 C15 1.386(2) . ?
C14 C19 1.387(2) . ?
C14 N1 1.398(2) . ?
C15 C16 1.381(3) . ?
C15 H15 1.04(2) . ?
C16 C17 1.369(3) . ?
C16 H16 1.03(2) . ?
C17 C18 1.400(3) . ?
C17 H17 0.93(3) . ?
C18 C19 1.376(3) . ?
C18 H18 0.984(19) . ?
C19 C20 1.511(2) . ?
C20 C23 1.522(2) . ?
C20 C22 1.539(3) . ?
C21 N1 1.449(2) . ?
C21 H211 0.98(3) . ?
C21 H212 0.99(2) . ?
C21 H213 1.01(3) . ?
C22 H221 1.01(2) . ?
C22 H222 1.12(2) . ?
C22 H223 0.98(2) . ?
C23 H231 1.03(2) . ?
C23 H232 1.02(2) . ?
C23 H233 0.97(3) . ?
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
_geom_torsion_publ_flag
O1 C1 C2 C3 179.52(17) . . . . ?
C10 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 178.24(18) . . . . ?
C2 C3 C4 C9 -1.2(3) . . . . ?
C3 C4 C5 C6 -179.68(18) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
C7 C8 C9 C10 179.31(17) . . . . ?
C3 C4 C9 C8 179.83(16) . . . . ?
C5 C4 C9 C8 0.4(2) . . . . ?
C3 C4 C9 C10 0.3(2) . . . . ?
C5 C4 C9 C10 -179.16(15) . . . . ?
O1 C1 C10 C9 179.73(14) . . . . ?
C2 C1 C10 C9 -2.3(2) . . . . ?
O1 C1 C10 C11 -3.5(2) . . . . ?
C2 C1 C10 C11 174.48(16) . . . . ?
C8 C9 C10 C1 -178.10(16) . . . . ?
C4 C9 C10 C1 1.4(2) . . . . ?
C8 C9 C10 C11 5.4(3) . . . . ?
C4 C9 C10 C11 -175.11(15) . . . . ?
C1 C10 C11 C12 8.8(3) . . . . ?
C9 C10 C11 C12 -174.60(17) . . . . ?
C10 C11 C12 C13 5.5(3) . . . . ?
C11 C12 C13 N1 -140.65(18) . . . . ?
C11 C12 C13 O1 -22.6(2) . . . . ?
C11 C12 C13 C20 101.1(2) . . . . ?
C19 C14 C15 C16 -0.7(3) . . . . ?
N1 C14 C15 C16 -177.04(17) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?
C17 C18 C19 C20 175.03(19) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
N1 C14 C19 C18 177.60(17) . . . . ?
C15 C14 C19 C20 -175.59(15) . . . . ?
N1 C14 C19 C20 1.32(18) . . . . ?
C18 C19 C20 C23 45.2(3) . . . . ?
C14 C19 C20 C23 -139.00(17) . . . . ?
C18 C19 C20 C22 -77.0(2) . . . . ?
C14 C19 C20 C22 98.78(17) . . . . ?
C18 C19 C20 C13 166.76(19) . . . . ?
C14 C19 C20 C13 -17.47(16) . . . . ?
N1 C13 C20 C19 26.54(15) . . . . ?
O1 C13 C20 C19 -85.74(13) . . . . ?
C12 C13 C20 C19 149.93(13) . . . . ?
N1 C13 C20 C23 149.80(15) . . . . ?
O1 C13 C20 C23 37.52(18) . . . . ?
C12 C13 C20 C23 -86.81(18) . . . . ?
N1 C13 C20 C22 -87.50(16) . . . . ?
O1 C13 C20 C22 160.22(13) . . . . ?
C12 C13 C20 C22 35.89(18) . . . . ?
C15 C14 N1 C21 -23.3(2) . . . . ?
C19 C14 N1 C21 160.00(15) . . . . ?
C15 C14 N1 C13 -165.95(16) . . . . ?
C19 C14 N1 C13 17.38(17) . . . . ?
O1 C13 N1 C14 86.81(14) . . . . ?
C12 C13 N1 C14 -152.59(14) . . . . ?
C20 C13 N1 C14 -27.63(15) . . . . ?
O1 C13 N1 C21 -56.39(18) . . . . ?
C12 C13 N1 C21 64.2(2) . . . . ?
C20 C13 N1 C21 -170.83(15) . . . . ?
C10 C1 O1 C13 -16.1(2) . . . . ?
C2 C1 O1 C13 165.80(15) . . . . ?
N1 C13 O1 C1 149.78(13) . . . . ?
C12 C13 O1 C1 27.56(19) . . . . ?
C20 C13 O1 C1 -99.63(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2010795
