#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/39/2103943.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_2103943
loop_
_publ_author_name
'Turowska-Tyrk, Ilona'
_publ_section_title
;
 Monitoring structural transformations in crystals. 5. A topotactic [2
 + 2]-photodimerization reaction
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              670
_journal_page_last               675
_journal_paper_doi               10.1107/S0108768103014484
_journal_volume                  59
_journal_year                    2003
_chemical_formula_sum            'C19 H17 Cl O'
_chemical_formula_weight         296.78
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.59(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.951(7)
_cell_length_b                   10.590(4)
_cell_length_c                   8.803(3)
_cell_measurement_reflns_used    763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17
_cell_measurement_theta_min      5
_cell_volume                     1529.3(10)
_computing_cell_refinement       'Kuma KM4CCD software 1998'
_computing_data_collection       'Kuma KM4CCD software 1998'
_computing_data_reduction        'Kuma KM4CCD software 1998'
_computing_molecular_graphics    'ORTEP-3 1997'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Kuma KM4CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7490
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         5.58
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.9641
_exptl_absorpt_correction_T_min  0.8507
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.1564
_refine_ls_R_factor_gt           0.0900
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0642P)²+0.6021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.2208
_reflns_number_gt                1724
_reflns_number_total             2946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk0133.cif
_cod_data_source_block           54D
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.6021P] where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.0642P)^2^+0.6021P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2103943
_cod_database_fobs_code          2103943
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1M 0.9024(14) 0.233(2) 0.957(2) 0.079(5) Uani d PDU 0.456(6) A 1 O
C1M 0.9109(9) 0.1699(15) 0.8452(18) 0.055(4) Uani d PDU 0.456(6) A 1 C
C2M 0.8405(12) 0.112(3) 0.722(3) 0.055(4) Uani d PDU 0.456(6) A 1 C
H2M 0.8332 0.1664 0.6294 0.067 Uiso calc PR 0.456(6) A 1 H
C3M 0.8726(12) -0.013(2) 0.678(2) 0.058(4) Uani d PDU 0.456(6) A 1 C
H3M1 0.8459 -0.0365 0.5704 0.069 Uiso calc PR 0.456(6) A 1 H
H3M2 0.8653 -0.0804 0.7477 0.069 Uiso calc PR 0.456(6) A 1 H
C4M 0.9646(13) 0.016(2) 0.696(2) 0.055(4) Uani d PDU 0.456(6) A 1 C
H4M1 0.9965 -0.0610 0.7211 0.066 Uiso calc PR 0.456(6) A 1 H
H4M2 0.9730 0.0504 0.5996 0.066 Uiso calc PR 0.456(6) A 1 H
C5M 0.9901(5) 0.1101(8) 0.8280(8) 0.055(2) Uani d PDU 0.456(6) A 1 C
C6M 0.7592(13) 0.114(4) 0.766(3) 0.072(5) Uani d PDU 0.456(6) A 1 C
H6M1 0.7572 0.0437 0.8354 0.086 Uiso calc PR 0.456(6) A 1 H
H6M2 0.7545 0.1914 0.8212 0.086 Uiso calc PR 0.456(6) A 1 H
C7M 0.6897(17) 0.104(3) 0.624(4) 0.064(4) Uani d PDU 0.456(6) A 1 C
C8M 0.6480(18) -0.007(3) 0.584(3) 0.077(5) Uani d PDU 0.456(6) A 1 C
H8M 0.6626 -0.0767 0.6503 0.093 Uiso calc PR 0.456(6) A 1 H
C9M 0.586(2) -0.020(3) 0.451(3) 0.083(5) Uani d PDU 0.456(6) A 1 C
H9M 0.5587 -0.0970 0.4276 0.100 Uiso calc PR 0.456(6) A 1 H
C10M 0.563(3) 0.082(3) 0.353(4) 0.080(4) Uani d PDU 0.456(6) A 1 C
C11M 0.6034(11) 0.195(2) 0.390(3) 0.067(4) Uani d PDU 0.456(6) A 1 C
H11M 0.5878 0.2649 0.3250 0.080 Uiso calc PR 0.456(6) A 1 H
C12M 0.6670(11) 0.207(2) 0.524(3) 0.061(4) Uani d PDU 0.456(6) A 1 C
H12M 0.6945 0.2834 0.5469 0.074 Uiso calc PR 0.456(6) A 1 H
Cl1M 0.4851(7) 0.0686(16) 0.1840(13) 0.110(2) Uani d PDU 0.456(6) A 1 Cl
C13M 1.0605(5) 0.1557(7) 0.9044(9) 0.059(2) Uani d PDU 0.456(6) A 1 C
H13M 1.0573 0.2182 0.9769 0.071 Uiso calc PR 0.456(6) A 1 H
C14M 1.1446(5) 0.1250(9) 0.8957(11) 0.055(2) Uani d PDU 0.456(6) A 1 C
C15M 1.2085(8) 0.1901(12) 0.9913(15) 0.057(4) Uani d PDU 0.456(6) A 1 C
H15M 1.1983 0.2483 1.0632 0.068 Uiso calc PR 0.456(6) A 1 H
C16M 1.2870(9) 0.1697(18) 0.982(3) 0.081(4) Uani d PDU 0.456(6) A 1 C
H16M 1.3289 0.2156 1.0469 0.097 Uiso calc PR 0.456(6) A 1 H
C17M 1.3061(8) 0.0842(19) 0.879(2) 0.084(3) Uani d PDU 0.456(6) A 1 C
H17M 1.3598 0.0676 0.8782 0.100 Uiso calc PR 0.456(6) A 1 H
C18M 1.2410(12) 0.023(2) 0.776(2) 0.080(4) Uani d PDU 0.456(6) A 1 C
H18M 1.2506 -0.0291 0.6980 0.096 Uiso calc PR 0.456(6) A 1 H
C19M 1.1626(8) 0.0405(10) 0.7909(12) 0.060(2) Uani d PDU 0.456(6) A 1 C
H19M 1.1206 -0.0066 0.7277 0.072 Uiso calc PR 0.456(6) A 1 H
O1D 0.9129(13) 0.2395(19) 0.957(2) 0.093(5) Uani d PDU 0.544(6) A 2 O
C1D 0.9037(8) 0.1427(11) 0.8776(15) 0.055(3) Uani d PDU 0.544(6) A 2 C
C2D 0.8364(10) 0.133(2) 0.726(3) 0.058(3) Uani d PDU 0.544(6) A 2 C
H2D 0.8401 0.2054 0.6594 0.070 Uiso calc PR 0.544(6) A 2 H
C3D 0.8601(11) 0.0128(16) 0.649(2) 0.057(4) Uani d PDU 0.544(6) A 2 C
H3D1 0.8486 0.0225 0.5364 0.069 Uiso calc PR 0.544(6) A 2 H
H3D2 0.8306 -0.0600 0.6732 0.069 Uiso calc PR 0.544(6) A 2 H
C4D 0.9528(10) -0.0022(18) 0.7218(15) 0.058(4) Uani d PDU 0.544(6) A 2 C
H4D1 0.9695 -0.0894 0.7166 0.070 Uiso calc PR 0.544(6) A 2 H
H4D2 0.9837 0.0505 0.6676 0.070 Uiso calc PR 0.544(6) A 2 H
C5D 0.9648(4) 0.0392(6) 0.8885(7) 0.0547(17) Uani d PDU 0.544(6) . 2 C
C6D 0.7515(11) 0.131(3) 0.757(3) 0.067(4) Uani d PDU 0.544(6) A 2 C
H6D1 0.7484 0.0605 0.8257 0.081 Uiso calc PR 0.544(6) A 2 H
H6D2 0.7444 0.2079 0.8120 0.081 Uiso calc PR 0.544(6) A 2 H
C7D 0.6835(14) 0.120(2) 0.613(3) 0.064(3) Uani d PDU 0.544(6) A 2 C
C8D 0.6547(15) 0.005(2) 0.552(3) 0.081(5) Uani d PDU 0.544(6) A 2 C
H8D 0.6783 -0.0682 0.6017 0.097 Uiso calc PR 0.544(6) A 2 H
C9D 0.5920(17) -0.006(2) 0.418(3) 0.089(6) Uani d PDU 0.544(6) A 2 C
H9D 0.5732 -0.0849 0.3795 0.107 Uiso calc PR 0.544(6) A 2 H
C10D 0.558(2) 0.102(2) 0.344(4) 0.085(4) Uani d PDU 0.544(6) A 2 C
C11D 0.5836(10) 0.2189(19) 0.402(2) 0.072(4) Uani d PDU 0.544(6) A 2 C
H11D 0.5596 0.2917 0.3519 0.086 Uiso calc PR 0.544(6) A 2 H
C12D 0.6459(8) 0.2267(17) 0.536(2) 0.061(3) Uani d PDU 0.544(6) A 2 C
H12D 0.6634 0.3060 0.5758 0.073 Uiso calc PR 0.544(6) A 2 H
Cl1D 0.4807(8) 0.0944(16) 0.1747(14) 0.164(5) Uani d PDU 0.544(6) A 2 Cl
C13D 1.0474(4) 0.0703(6) 1.0000(6) 0.0532(17) Uani d PDU 0.544(6) . 2 C
H13D 1.0406 0.1497 1.0526 0.064 Uiso calc PR 0.544(6) A 2 H
C14D 1.1251(5) 0.0819(8) 0.9485(9) 0.061(2) Uani d PDU 0.544(6) A 2 C
C15D 1.1790(8) 0.1772(13) 1.0152(15) 0.071(3) Uani d PDU 0.544(6) A 2 C
H15D 1.1647 0.2344 1.0838 0.085 Uiso calc PR 0.544(6) A 2 H
C16D 1.2536(9) 0.1875(16) 0.9803(19) 0.087(5) Uani d PDU 0.544(6) A 2 C
H16D 1.2895 0.2508 1.0275 0.105 Uiso calc PR 0.544(6) A 2 H
C17D 1.2754(8) 0.1068(16) 0.878(2) 0.090(3) Uani d PDU 0.544(6) A 2 C
H17D 1.3258 0.1153 0.8552 0.108 Uiso calc PR 0.544(6) A 2 H
C18D 1.2221(10) 0.011(2) 0.807(2) 0.078(3) Uani d PDU 0.544(6) A 2 C
H18D 1.2366 -0.0449 0.7376 0.094 Uiso calc PR 0.544(6) A 2 H
C19D 1.1474(6) 0.0007(9) 0.8429(10) 0.064(2) Uani d PDU 0.544(6) A 2 C
H19D 1.1113 -0.0621 0.7949 0.077 Uiso calc PR 0.544(6) A 2 H
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_3
_geom_angle
O1M C1M C2M . 124.0(13)
O1M C1M C5M . 126.2(13)
C2M C1M C5M . 108.4(12)
C6M C2M C1M . 114.6(17)
C6M C2M C3M . 119(2)
C1M C2M C3M . 105.4(13)
C2M C3M C4M . 102.3(14)
C5M C4M C3M . 107.3(12)
C13M C5M C4M . 133.5(10)
C13M C5M C1M . 120.5(9)
C4M C5M C1M . 105.2(11)
C7M C6M C2M . 112(2)
C8M C7M C12M . 117.8(17)
C8M C7M C6M . 121(2)
C12M C7M C6M . 121(2)
C9M C8M C7M . 122.6(19)
C8M C9M C10M . 119.3(19)
C11M C10M C9M . 119.5(16)
C11M C10M Cl1M . 120.2(17)
C9M C10M Cl1M . 120.3(17)
C10M C11M C12M . 120.8(17)
C11M C12M C7M . 120.1(17)
C5M C13M C14M . 131.1(7)
C19M C14M C15M . 117.6(9)
C19M C14M C13M . 123.8(9)
C15M C14M C13M . 118.5(9)
C16M C15M C14M . 120.6(14)
C15M C16M C17M . 122.5(15)
C16M C17M C18M . 116.9(12)
C19M C18M C17M . 120.1(15)
C14M C19M C18M . 122.0(13)
O1D C1D C5D . 126.2(11)
O1D C1D C2D . 120.9(12)
C5D C1D C2D . 111.0(10)
C1D C2D C6D . 112.0(16)
C1D C2D C3D . 102.7(12)
C6D C2D C3D . 115.5(18)
C2D C3D C4D . 104.8(11)
C5D C4D C3D . 104.3(10)
C1D C5D C4D . 103.4(9)
C1D C5D C13D . 113.0(7)
C4D C5D C13D . 124.7(8)
C1D C5D C13D 3_757 112.6(7)
C4D C5D C13D 3_757 113.0(9)
C13D C5D C13D 3_757 90.1(4)
C7D C6D C2D . 114.2(17)
C8D C7D C12D . 117.2(14)
C8D C7D C6D . 121.6(17)
C12D C7D C6D . 121.2(18)
C9D C8D C7D . 121.9(16)
C10D C9D C8D . 119.0(16)
C11D C10D C9D . 120.9(14)
C11D C10D Cl1D . 118.1(15)
C9D C10D Cl1D . 121.0(15)
C12D C11D C10D . 118.8(14)
C11D C12D C7D . 122.1(14)
C14D C13D C5D . 123.6(5)
C14D C13D C5D 3_757 120.9(6)
C5D C13D C5D 3_757 89.9(4)
C19D C14D C15D . 118.2(8)
C19D C14D C13D . 124.1(7)
C15D C14D C13D . 117.7(8)
C16D C15D C14D . 120.4(13)
C17D C16D C15D . 121.1(13)
C16D C17D C18D . 119.9(11)
C19D C18D C17D . 119.0(13)
C18D C19D C14D . 121.5(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1M C1M . 1.228(16)
C1M C2M . 1.521(15)
C1M C5M . 1.526(14)
C2M C6M . 1.520(16)
C2M C3M . 1.526(16)
C3M C4M . 1.556(17)
C4M C5M . 1.509(15)
C5M C13M . 1.305(9)
C6M C7M . 1.485(15)
C7M C8M . 1.377(16)
C7M C12M . 1.392(16)
C8M C9M . 1.374(16)
C9M C10M . 1.378(16)
C10M C11M . 1.378(16)
C10M Cl1M . 1.730(15)
C11M C12M . 1.387(15)
C13M C14M . 1.484(11)
C14M C19M . 1.374(12)
C14M C15M . 1.377(14)
C15M C16M . 1.372(13)
C16M C17M . 1.373(16)
C17M C18M . 1.395(16)
C18M C19M . 1.380(16)
O1D C1D . 1.227(15)
C1D C5D . 1.494(12)
C1D C2D . 1.526(15)
C2D C6D . 1.530(14)
C2D C3D . 1.538(14)
C3D C4D . 1.547(14)
C4D C5D . 1.496(12)
C5D C13D . 1.530(8)
C5D C13D 3_757 1.567(9)
C6D C7D . 1.490(13)
C7D C8D . 1.376(14)
C7D C12D . 1.385(14)
C8D C9D . 1.373(14)
C9D C10D . 1.373(15)
C10D C11D . 1.371(15)
C10D Cl1D . 1.714(14)
C11D C12D . 1.370(13)
C13D C14D . 1.502(9)
C13D C5D 3_757 1.567(9)
C14D C19D . 1.386(11)
C14D C15D . 1.389(13)
C15D C16D . 1.379(12)
C16D C17D . 1.359(15)
C17D C18D . 1.395(15)
C18D C19D . 1.384(13)
