#------------------------------------------------------------------------------
#$Date: 2017-08-14 11:54:45 +0100 (Mon, 14 Aug 2017) $
#$Revision: 199742 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/50/2005050.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2005050
loop_
_publ_author_name
'Aldoshin, S.'
'Chuev, I.'
'Philipenko, O.'
'Pozzo, J. L.'
'Lokshin, V.'
'P\`epe, G.'
'Samat, A.'
_publ_section_title
;
 Photochromic Pyrido-Annelated 2,2-Dimethylchromene
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1537
_journal_page_last               1539
_journal_paper_doi               10.1107/S0108270195016192
_journal_volume                  52
_journal_year                    1996
_chemical_formula_analytical     'C14 H15 N O2'
_chemical_formula_moiety         'C14 H13 N O , H2 O'
_chemical_formula_structural     'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.28
_chemical_name_common            Chromene
_chemical_name_systematic
;
8,8-dimethyl-[8H]-pyrano[3,2-f]quinolene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.05(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.123(4)
_cell_length_b                   11.484(2)
_cell_length_c                   9.2200(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      10.0
_cell_volume                     2438.8(7)
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'KM-4 diffractometer'
_diffrn_measurement_method       \q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_sigmaI/netI    0.2606
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1826
_diffrn_reflns_theta_max         23.03
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.957
_refine_ls_goodness_of_fit_obs   1.188
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         1700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_restrained_S_obs      1.188
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_obs          0.0405
_refine_ls_shift/esd_max         -0.085
_refine_ls_shift/esd_mean        0.04
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.047
_refine_ls_wR_factor_obs         0.047
_reflns_number_observed          922
_reflns_number_total             1700
_reflns_observed_criterion       refl_obs_if_I_>_2.0_sigma(I)
_cod_data_source_file            pa1202.cif
_cod_data_source_block           aldoshin_structure
_cod_depositor_comments
;
 Adding the _atom_site_type_symbol data item.

 Antanas Vaitkus,
 2017-08-14

 Changing the _atom_site_occupancy data item value from '.' to '1'
 for all fully occupied atom sites.

 Antanas Vaitkus,
 2017-02-10

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2005050
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z-1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0408(12) 0.0624(12) 0.0497(12) 0.0098(9) 0.0040(9) -0.0039(9)
N1 0.0430(15) 0.066(2) 0.056(2) -0.0143(13) 0.0016(11) -0.0003(12)
C1 0.039(2) 0.055(2) 0.058(2) -0.0049(14) 0.0138(13) -0.0046(12)
C2 0.053(2) 0.055(2) 0.063(2) 0.006(2) 0.017(2) -0.0070(15)
C3 0.054(2) 0.049(2) 0.058(2) 0.0103(15) 0.0130(15) 0.0001(14)
C4 0.047(2) 0.0353(13) 0.0371(15) 0.0012(12) 0.0091(12) 0.0033(11)
C5 0.037(2) 0.0402(14) 0.039(2) -0.0030(12) 0.0062(11) 0.0009(11)
C6 0.045(2) 0.0415(15) 0.048(2) 0.0050(13) 0.0056(13) 0.0001(12)
C7 0.044(2) 0.0388(15) 0.053(2) 0.0015(14) 0.0110(14) -0.0042(13)
C8 0.038(2) 0.0399(14) 0.047(2) -0.0097(13) 0.0073(12) 0.0018(12)
C9 0.049(2) 0.0376(14) 0.0366(15) -0.0047(12) 0.0075(12) 0.0053(12)
C10 0.063(2) 0.053(2) 0.049(2) 0.0006(14) 0.004(2) 0.016(2)
C11 0.063(2) 0.075(2) 0.054(2) -0.003(2) -0.008(2) 0.026(2)
C12 0.049(2) 0.080(2) 0.053(2) -0.015(2) 0.000(2) 0.008(2)
C13 0.056(2) 0.070(2) 0.084(3) -0.018(2) 0.011(2) 0.004(2)
C14 0.045(2) 0.075(3) 0.085(3) -0.009(2) 0.007(2) -0.012(2)
OW 0.057(2) 0.097(2) 0.075(2) -0.0068(14) 0.0030(13) 0.008(2)
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_Wyckoff_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
O1 O d 0.13782(7) 0.3792(2) -0.5006(2) 5.10(6) Uani 1
N1 N d 0.37017(10) 0.4032(2) -0.3021(3) 5.53(7) Uani 1
C1 C d 0.09437(11) 0.3439(2) -0.4023(3) 5.01(8) Uani 1
C2 C d 0.11662(13) 0.2425(3) -0.3133(3) 5.66(8) Uani 1
C3 C d 0.17315(13) 0.2287(3) -0.2759(3) 5.29(8) Uani 1
C4 C d 0.21455(11) 0.3095(2) -0.3308(3) 3.95(7) Uani 1
C5 C d 0.19473(10) 0.3808(2) -0.4437(3) 3.86(7) Uani 1
C6 C d 0.23234(12) 0.4556(2) -0.5143(3) 4.46(7) Uani 1
C7 C d 0.28952(12) 0.4602(2) -0.4667(3) 4.48(7) Uani 1
C8 C d 0.31239(11) 0.3916(2) -0.3474(3) 4.15(7) Uani 1
C9 C d 0.27493(11) 0.3148(2) -0.2792(3) 4.08(7) Uani 1
C10 C d 0.30027(14) 0.2458(3) -0.1635(3) 5.49(8) Uani 1
C11 C d 0.3584(2) 0.2592(3) -0.1203(4) 6.52(10) Uani 1
C12 C d 0.39126(15) 0.3392(3) -0.1903(3) 6.07(9) Uani 1
C13 C d 0.0828(2) 0.4479(3) -0.3066(5) 6.95(10) Uani 1
C14 C d 0.04104(15) 0.3123(4) -0.5049(5) 6.81(10) Uani 1
OW O d 0.46867(12) 0.5390(3) -0.3869(3) 7.64(8) Uani 1
H2 H . 0.085(2) 0.186(4) -0.249(5) . . 1
H3 H . 0.188(2) 0.166(3) -0.190(4) . . 1
H6 H . 0.215(1) 0.503(2) -0.602(3) . . 1
H7 H . 0.318(1) 0.518(3) -0.515(3) . . 1
H10 H . 0.274(1) 0.189(3) -0.096(3) . . 1
H11 H . 0.375(2) 0.222(3) -0.035(4) . . 1
H12 H . 0.435(1) 0.345(2) -0.158(3) . . 1
H13 H . 0.066(1) 0.512(3) -0.375(3) . . 1
H131 H . 0.117(2) 0.474(3) -0.235(4) . . 1
H132 H . 0.052(1) 0.418(2) -0.229(3) . . 1
H14 H . 0.030(1) 0.379(3) -0.560(4) . . 1
H141 H . 0.009(2) 0.295(3) -0.445(4) . . 1
H142 H . 0.049(1) 0.241(3) -0.562(4) . . 1
HW1 H . 0.440(2) 0.502(4) -0.388(5) . . 1
HW2 H . 0.491(3) 0.539(5) -0.307(3) . . 1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .0033 .0016 International_Tables_Vol_C_Tables_4.2.6.8_and_6.1.1.4
H .0000 .0000 International_Tables_Vol_C_Tables_4.2.6.8_and_6.1.1.4
N .0061 .0033 International_Tables_Vol_C_Tables_4.2.6.8_and_6.1.1.4
O .0106 .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_publ_flag
C5 O1 C1 116.9(2) yes
C12 N1 C8 117.8(3) yes
O1 C1 C2 109.5(2) yes
O1 C1 C13 107.8(2) yes
C2 C1 C13 111.3(3) yes
O1 C1 C14 104.0(2) yes
C2 C1 C14 112.0(3) yes
C13 C1 C14 111.8(3) yes
C3 C2 C1 121.2(3) yes
C2 C3 C4 119.7(3) yes
C5 C4 C9 118.4(2) yes
C5 C4 C3 117.3(2) yes
C9 C4 C3 124.2(2) yes
C4 C5 O1 121.8(2) yes
C4 C5 C6 122.1(2) yes
O1 C5 C6 116.0(2) yes
C7 C6 C5 119.6(3) yes
C6 C7 C8 121.0(2) yes
N1 C8 C7 118.0(2) yes
N1 C8 C9 122.8(2) yes
C7 C8 C9 119.2(2) yes
C10 C9 C8 117.0(3) yes
C10 C9 C4 123.5(2) yes
C8 C9 C4 119.5(2) yes
C11 C10 C9 119.0(3) yes
C10 C11 C12 120.0(3) yes
N1 C12 C11 123.4(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.373(3) yes
O1 C1 1.468(3) yes
N1 C12 1.323(4) yes
N1 C8 1.371(3) yes
C1 C2 1.490(4) yes
C1 C13 1.523(4) yes
C1 C14 1.530(4) yes
C2 C3 1.332(4) yes
C3 C4 1.455(4) yes
C4 C5 1.371(4) yes
C4 C9 1.436(4) yes
C5 C6 1.420(4) yes
C6 C7 1.357(4) yes
C7 C8 1.417(4) yes
C8 C9 1.421(4) yes
C9 C10 1.414(4) yes
C10 C11 1.378(4) yes
C11 C12 1.387(5) yes