#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/12/2101245.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_2101245
loop_
_publ_author_name
'Crano, J.'
'Knowles, D.'
'Kwiatkowski, P.'
'Flood, T.'
'Ross, R.'
'Chiang, L.'
'Lasch, J.'
'Chadha, R.'
'Siuzdak, G.'
_publ_section_title
;
 Structure of three novel photochromic compounds; X-ray
 crystallographic and theoretical studies
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              772
_journal_page_last               779
_journal_paper_doi               10.1107/S0108768194005938
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C20 H22 N2 O3'
_chemical_formula_weight         338.4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 90.310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.151(2)
_cell_length_b                   12.090(4)
_cell_length_c                   24.836(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      40
_cell_measurement_theta_min      25
_cell_volume                     3648.5(15)
_diffrn_measurement_device       'Rigaku AFC-6R four-circle'
_diffrn_measurement_method       2θ-θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6159
_diffrn_reflns_theta_max         60.0
_diffrn_standards_decay_%        'not significant'
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_description       parallelepiped
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.43
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     451
_refine_ls_number_reflns         3106
_refine_ls_R_factor_obs          0.0630
_refine_ls_shift/esd_max         0.018
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F)+0.0004F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0794
_reflns_number_observed          3106
_reflns_number_total             5446
_reflns_observed_criterion       F>4.0\s(F)
_cod_data_source_file            st1087.cif
_cod_data_source_block           st1087a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^(F)+0.0004F^2^]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(F)+0.0004F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3648(2)
_cod_database_code               2101245
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(1A) .4845(2) .2124(2) .47590(10) .0470(10)
O(2A) .8234(3) .3291(3) .55430(10) .0730(10)
O(3A) .5232(3) .2295(3) .66510(10) .0660(10)
N(1A) .3272(3) .1265(3) .4415(2) .0530(10)
N(2A) .3950(3) .1825(3) .5789(2) .0510(10)
C(1A) .3056(4) .3665(6) .3584(3) .082(3)
C(2A) .3055(5) .3213(9) .3065(3) .110(4)
C(3A) .3126(5) .2105(10) .2984(3) .114(4)
C(4A) .3203(4) .1377(6) .3411(2) .086(3)
C(5A) .3212(3) .1834(5) .3920(2) .054(2)
C(6A) .3139(4) .2955(4) .4006(2) .055(2)
C(7A) .3157(4) .3168(4) .4606(2) .049(2)
C(8A) .3790(5) .4175(4) .4774(3) .080(2)
C(9A) .1947(5) .3281(5) .4805(3) .089(3)
C(10A) .3654(3) .2078(3) .4805(2) .045(2)
C(11A) .3748(5) .0162(4) .4435(2) .077(2)
C(12A) .3341(4) .1739(4) .5373(2) .053(2)
C(13A) .5019(3) .2246(3) .5717(2) .042(2)
C(14A) .5458(3) .2373(3) .5204(2) .0400(10)
C(15A) .6537(3) .2702(4) .5121(2) .048(2)
C(16A) .7178(4) .2923(4) .5569(2) .051(2)
C(17A) .6767(4) .2808(4) .6093(2) .050(2)
C(18A) .5703(4) .2454(4) .6163(2) .047(2)
C(19A) .8705(4) .3412(6) .5028(2) .087(3)
C(20A) .5898(5) .2437(7) .7117(2) .109(3)
O(1B) 1.0695(2) .0542(3) .24440(10) .0540(10)
O(2B) .9542(3) -.0181(4) .42370(10) .097(2)
O(3B) .6918(3) .0505(3) .2856(2) .0750(10)
N(1B) 1.1242(3) .1041(3) .1582(2) .0550(10)
N(2B) .8503(3) .0814(3) .2113(2) .058(2)
C(1B) 1.2704(5) -.1536(4) .1552(2) .070(2)
C(2B) 1.3776(4) -.1222(6) .1436(2) .081(3)
C(3B) 1.4038(5) -.0132(6) .1384(2) .084(3)
C(4B) 1.3262(4) .0684(5) .1429(2) .064(2)
C(5B) 1.2189(4) .0365(4) .1532(2) .047(2)
C(6B) 1.1917(4) -.0727(4) .1599(2) .051(2)
C(7B) 1.0705(4) -.0799(4) .1708(2) .051(2)
C(8B) 1.0397(5) -.1662(5) .2128(3) .105(3)
C(9B) 1.0087(5) -.1103(7) .1219(3) .120(4)
C(10B) 1.0433(3) .0387(4) .1876(2) .047(2)
C(11B) 1.1342(5) .2219(4) .1678(2) .078(2)
C(12B) .9268(4) .0754(4) .1772(2) .062(2)
C(13B) .8784(4) .0515(4) .2646(2) .045(2)
C(14B) .9858(4) .0391(4) .2807(2) .046(2)
C(15B) 1.0166(4) .0183(4) .3330(2) .058(2)
C(16B) .9350(5) .0073(5) .3703(2) .065(2)
C(17B) .8247(4) .0161(4) .3562(2) .062(2)
C(18B) .7966(4) .0382(4) .3040(2) .053(2)
C(19B) 1.0649(6) -.0401(8) .4390(3) .143(4)
C(20B) .6039(4) .0340(6) .3227(3) .102(3)
H1AA .3000 .4448 .3638 ?
H2AA .3001 .3699 .2761 ?
H3AA .3128 .1827 .2622 ?
H4AA .3246 .0593 .3356 ?
H8AA .4537 .4112 .4653 ?
H8AB .3783 .4237 .5159 ?
H8AC .3459 .4820 .4618 ?
H9AA .1534 .2640 .4699 ?
H9AB .1619 .3927 .4648 ?
H9AC .1943 .3345 .5190 ?
H11A .3732 -.0105 .4799 ?
H11B .4496 .0188 .4313 ?
H11C .3329 -.0325 .4208 ?
H12A .2620 .1433 .5423 ?
H15A .6829 .2777 .4765 ?
H17A .7225 .2972 .6398 ?
H19A .9446 .3676 .5064 ?
H19B .8280 .3934 .4823 ?
H19C .8707 .2713 .4846 ?
H20A .5468 .2301 .7433 ?
H20B .6173 .3180 .7125 ?
H20C .6505 .1929 .7107 ?
H1BA 1.2515 -.2301 .1596 ?
H2BB 1.4336 -.1774 .1393 ?
H3BA 1.4788 .0069 .1315 ?
H4BA 1.3457 .1448 .1391 ?
H8BA 1.0773 -.1509 .2461 ?
H8BB 1.0611 -.2377 .1999 ?
H8BC .9617 -.1649 .2186 ?
H9BA 1.0244 -.0580 .0939 ?
H9BB .9312 -.1100 .1293 ?
H9BC 1.0307 -.1828 .1105 ?
H11D 1.0622 .2542 .1701 ?
H11E 1.1739 .2555 .1388 ?
H11F 1.1732 .2340 .2010 ?
H12B .9088 .0960 .1408 ?
H15B 1.0927 .0121 .3431 ?
H17B .7687 .0069 .3829 ?
H19D 1.0675 -.0564 .4768 ?
H19G 1.1104 .0229 .4317 ?
H19E 1.0912 -.1025 .4190 ?
H20G .5346 .0450 .3047 ?
H20D .6109 .0859 .3518 ?
H20E .6073 -.0399 .3367 ?
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
C(10A) O(1A) C(14A) 118.8(3) yes
C(18A) O(3A) C(20A) 118.0(4) yes
C(5A) N(1A) C(11A) 119.7(4) yes
C(12A) N(2A) C(13A) 117.3(4) yes
C(1A) C(2A) C(3A) 121.5(8) yes
C(3A) C(4A) C(5A) 116.5(7) yes
N(1A) C(5A) C(6A) 110.3(4) yes
C(1A) C(6A) C(5A) 120.4(5) yes
C(5A) C(6A) C(7A) 108.8(4) yes
C(6A) C(7A) C(9A) 108.5(4) yes
C(6A) C(7A) C(10A) 100.1(4) yes
C(9A) C(7A) C(10A) 110.1(4) yes
O(1A) C(10A) C(7A) 109.4(3) yes
O(1A) C(10A) C(12A) 109.8(3) yes
C(7A) C(10A) C(12A) 115.6(4) yes
N(2A) C(13A) C(14A) 121.1(4) yes
C(14A) C(13A) C(18A) 118.3(4) yes
O(1A) C(14A) C(15A) 117.1(4) yes
C(14A) C(15A) C(16A) 117.8(4) yes
O(2A) C(16A) C(17A) 114.6(4) yes
C(16A) C(17A) C(18A) 119.2(4) yes
O(3A) C(18A) C(17A) 124.0(4) yes
C(10B) O(1B) C(14B) 117.4(3) yes
C(18B) O(3B) C(20B) 118.0(4) yes
C(5B) N(1B) C(11B) 121.0(4) yes
C(12B) N(2B) C(13B) 116.0(4) yes
C(1B) C(2B) C(3B) 120.3(6) yes
C(3B) C(4B) C(5B) 117.6(5) yes
N(1B) C(5B) C(6B) 110.5(4) yes
C(16A) O(2A) C(19A) 117.6(4) yes
C(5A) N(1A) C(10A) 105.4(4) yes
C(10A) N(1A) C(11A) 118.2(4) yes
C(2A) C(1A) C(6A) 117.6(7) yes
C(2A) C(3A) C(4A) 121.4(7) yes
N(1A) C(5A) C(4A) 127.1(5) yes
C(4A) C(5A) C(6A) 122.6(5) yes
C(1A) C(6A) C(7A) 130.8(5) yes
C(6A) C(7A) C(8A) 114.7(4) yes
C(8A) C(7A) C(9A) 108.9(4) yes
C(8A) C(7A) C(10A) 114.2(4) yes
O(1A) C(10A) N(1A) 106.7(3) yes
N(1A) C(10A) C(7A) 104.1(3) yes
N(1A) C(10A) C(12A) 110.8(4) yes
N(2A) C(12A) C(10A) 125.8(4) yes
N(2A) C(13A) C(18A) 120.4(4) yes
O(1A) C(14A) C(13A) 120.5(4) yes
C(13A) C(14A) C(15A) 122.3(4) yes
O(2A) C(16A) C(15A) 123.6(4) yes
C(15A) C(16A) C(17A) 121.7(4) yes
O(3A) C(18A) C(13A) 115.4(4) yes
C(13A) C(18A) C(17A) 120.6(4) yes
C(16B) O(2B) C(19B) 117.0(4) yes
C(5B) N(1B) C(10B) 106.2(4) yes
C(10B) N(1B) C(11B) 120.5(4) yes
C(2B) C(1B) C(6B) 118.4(5) yes
C(2B) C(3B) C(4B) 121.9(5) yes
N(1B) C(5B) C(4B) 128.4(4) yes
C(4B) C(5B) C(6B) 121.2(4) yes
C(1B) C(6B) C(5B) 120.6(4) yes
C(5B) C(6B) C(7B) 108.3(4) yes
C(6B) C(7B) C(9B) 111.3(4) yes
C(6B) C(7B) C(10B) 102.0(4) yes
C(9B) C(7B) C(10B) 110.4(4) yes
O(1B) C(10B) C(7B) 109.8(4) yes
O(1B) C(10B) C(12B) 109.2(4) yes
C(7B) C(10B) C(12B) 115.7(4) yes
N(2B) C(13B) C(14B) 121.8(4) yes
C(14B) C(13B) C(18B) 117.2(4) yes
O(1B) C(14B) C(15B) 116.5(4) yes
C(14B) C(15) C(16B) 117.6(5) yes
O(2B) C(16B) C(17B) 114.7(5) yes
C(16B) C(17B) C(18B) 119.4(5) yes
O(3B) C(18B) C(17B) 124.7(4) yes
C(1B) C(6B) C(7B) 131.1(5) yes
C(6B) C(7B) C(8B) 114.1(4) yes
C(8B) C(7B) C(9B) 105.5(5) yes
C(8B) C(7B) C(10B) 113.6(4) yes
O(1B) C(10B) N(1B) 105.7(3) yes
N(1B) C(10B) C(7B) 103.0(3) yes
N(1B) C(10B) C(12B) 112.9(4) yes
N(2B) C(12B) C(10B) 126.6(4) yes
N(2B) C(13B) C(18B) 120.9(4) yes
O(1B) C(14B) C(13B) 119.9(4) yes
C(13B) C(14B) C(15B) 123.4(4) yes
O(2B) C(16B) C(15B) 123.6(5) yes
C(15B) C(16B) C(17B) 121.6(5) yes
O(3B) C(18B) C(13B) 114.6(4) yes
C(13B) C(18B) C(17B) 120.6(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1A) C(10A) 1.454(5) yes
O(2A) C(16A) 1.360(6) yes
O(3A) C(18A) 1.358(5) yes
N(1A) C(5A) 1.412(6) yes
N(1A) C(11A) 1.456(6) yes
N(2A) C(13A) 1.407(5) yes
C(1A) C(6A) 1.361(9) yes
C(3A) C(4A) 1.382(11) yes
C(5A) C(6A) 1.377(8) yes
C(7A) C(8A) 1.500(7) yes
C(7A) C(10A) 1.532(6) yes
C(13A) C(14A) 1.391(6) yes
C(14A) C(15A) 1.387(6) yes
C(16A) C(17A) 1.402(7) yes
O(1B) C(10B) 1.456(5) yes
O(2B) C(16B) 1.380(6) yes
O(3B) C(18B) 1.359(6) yes
N(1B) C(5B) 1.418(6) yes
N(1B) C(11B) 1.451(7) yes
N(2B) C(13B) 1.412(6) yes
C(1B) C(6B) 1.374(7) yes
C(3B) C(4B) 1.370(8) yes
C(5B) C(6B) 1.373(7) yes
C(7B) C(8B) 1.524(8) yes
C(7B) C(10B) 1.532(7) yes
C(13B) C(14B) 1.371(6) yes
C(14B) C(15B) 1.374(6) yes
C(16B) C(17B) 1.387(8) yes
O(1A) C(14A) 1.364(5) yes
O(2A) C(19A) 1.413(6) yes
O(3A) C(20A) 1.419(6) yes
N(1A) C(10A) 1.456(6) yes
N(2A) C(12A) 1.274(6) yes
C(1A) C(2A) 1.400(11) yes
C(2A) C(3A) 1.359(16) yes
C(4A) C(5A) 1.380(8) yes
C(6A) C(7A) 1.512(7) yes
C(7A) C(9A) 1.560(7) yes
C(10A) C(12A) 1.518(6) yes
C(13A) C(18A) 1.405(6) yes
C(15A) C(16A) 1.380(6) yes
C(17A) C(18A) 1.374(6) yes
O(1B) C(14B) 1.375(5) yes
O(2B) C(19B) 1.420(9) yes
O(3B) C(20B) 1.429(7) yes
N(1B) C(10B) 1.460(6) yes
N(2B) C(12B) 1.263(6) yes
C(1B) C(2B) 1.388(8) yes
C(2B) C(3B) 1.363(10) yes
C(4B) C(5B) 1.385(7) yes
C(6B) C(7B) 1.501(7) yes
C(7B) C(9B) 1.471(8) yes
C(10B) C(12B) 1.505(6) yes
C(13B) C(18B) 1.408(7) yes
C(15B) C(16B) 1.367(7) yes
C(17B) C(18B) 1.366(7) yes
