#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/39/2103942.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_2103942
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                 104.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.961(6)
_cell_length_b                   10.581(4)
_cell_length_c                   8.803(3)
_cell_measurement_reflns_used    767
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      5
_cell_volume                     1529.1(9)
_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  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0746
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7414
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_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         0.147
_refine_diff_density_min         -0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.1650
_refine_ls_R_factor_gt           0.0931
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0569P)²+0.7753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1818
_refine_ls_wR_factor_ref         0.2209
_reflns_number_gt                1689
_reflns_number_total             2949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk0133.cif
_cod_data_source_block           50D
_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^)+(0.0569P)^2^+0.7753P] 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^)+(0.0569P)^2^+0.7753P] 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               2103942
_cod_database_fobs_code          2103942
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 0.9026(16) 0.234(3) 0.955(3) 0.082(5) Uani d PDU 0.496(6) A 1 O
C1M 0.9120(9) 0.1690(15) 0.8458(19) 0.056(4) Uani d PDU 0.496(6) A 1 C
C2M 0.8420(11) 0.117(3) 0.717(3) 0.056(3) Uani d PDU 0.496(6) A 1 C
H2M 0.8370 0.1712 0.6250 0.067 Uiso calc PR 0.496(6) A 1 H
C3M 0.8733(12) -0.011(2) 0.677(2) 0.059(4) Uani d PDU 0.496(6) A 1 C
H3M1 0.8473 -0.0356 0.5698 0.071 Uiso calc PR 0.496(6) A 1 H
H3M2 0.8638 -0.0766 0.7477 0.071 Uiso calc PR 0.496(6) A 1 H
C4M 0.9658(12) 0.013(2) 0.699(2) 0.058(4) Uani d PDU 0.496(6) A 1 C
H4M1 0.9963 -0.0649 0.7281 0.070 Uiso calc PR 0.496(6) A 1 H
H4M2 0.9763 0.0440 0.6022 0.070 Uiso calc PR 0.496(6) A 1 H
C5M 0.9904(4) 0.1104(7) 0.8282(8) 0.0531(19) Uani d PDU 0.496(6) A 1 C
C6M 0.7606(12) 0.121(5) 0.759(3) 0.073(4) Uani d PDU 0.496(6) A 1 C
H6M1 0.7585 0.0524 0.8316 0.087 Uiso calc PR 0.496(6) A 1 H
H6M2 0.7563 0.1998 0.8127 0.087 Uiso calc PR 0.496(6) A 1 H
C7M 0.6900(15) 0.110(3) 0.620(4) 0.064(3) Uani d PDU 0.496(6) A 1 C
C8M 0.6475(15) -0.002(3) 0.585(3) 0.077(4) Uani d PDU 0.496(6) A 1 C
H8M 0.6627 -0.0709 0.6518 0.093 Uiso calc PR 0.496(6) A 1 H
C9M 0.5834(14) -0.016(3) 0.454(2) 0.079(4) Uani d PDU 0.496(6) A 1 C
H9M 0.5554 -0.0920 0.4343 0.094 Uiso calc PR 0.496(6) A 1 H
C10M 0.561(2) 0.084(3) 0.352(4) 0.086(4) Uani d PDU 0.496(6) A 1 C
C11M 0.6018(14) 0.198(2) 0.386(3) 0.070(4) Uani d PDU 0.496(6) A 1 C
H11M 0.5869 0.2661 0.3186 0.084 Uiso calc PR 0.496(6) A 1 H
C12M 0.6643(15) 0.211(3) 0.520(3) 0.068(5) Uani d PDU 0.496(6) A 1 C
H12M 0.6898 0.2888 0.5432 0.082 Uiso calc PR 0.496(6) A 1 H
Cl1M 0.4845(8) 0.0680(17) 0.1819(13) 0.112(2) Uani d PDU 0.496(6) A 1 Cl
C13M 1.0618(4) 0.1555(7) 0.9060(8) 0.055(2) Uani d PDU 0.496(6) A 1 C
H13M 1.0590 0.2172 0.9798 0.066 Uiso calc PR 0.496(6) A 1 H
C14M 1.1439(5) 0.1249(8) 0.8958(10) 0.053(2) Uani d PDU 0.496(6) A 1 C
C15M 1.2074(8) 0.1885(13) 0.9937(17) 0.065(4) Uani d PDU 0.496(6) A 1 C
H15M 1.1966 0.2467 1.0650 0.078 Uiso calc PR 0.496(6) A 1 H
C16M 1.2867(9) 0.1675(16) 0.988(2) 0.080(4) Uani d PDU 0.496(6) A 1 C
H16M 1.3283 0.2114 1.0566 0.096 Uiso calc PR 0.496(6) A 1 H
C17M 1.3066(8) 0.0834(16) 0.884(2) 0.086(3) Uani d PDU 0.496(6) A 1 C
H17M 1.3604 0.0697 0.8814 0.104 Uiso calc PR 0.496(6) A 1 H
C18M 1.2429(11) 0.020(3) 0.782(3) 0.080(4) Uani d PDU 0.496(6) A 1 C
H18M 1.2536 -0.0366 0.7091 0.096 Uiso calc PR 0.496(6) A 1 H
C19M 1.1637(8) 0.0407(10) 0.7906(12) 0.063(2) Uani d PDU 0.496(6) A 1 C
H19M 1.1220 -0.0036 0.7227 0.075 Uiso calc PR 0.496(6) A 1 H
O1D 0.9143(17) 0.241(3) 0.958(4) 0.093(5) Uani d PDU 0.504(6) A 2 O
C1D 0.9041(9) 0.1444(14) 0.8790(19) 0.057(4) Uani d PDU 0.504(6) A 2 C
C2D 0.8346(12) 0.129(3) 0.732(3) 0.061(4) Uani d PDU 0.504(6) A 2 C
H2D 0.8360 0.2025 0.6646 0.074 Uiso calc PR 0.504(6) A 2 H
C3D 0.8595(13) 0.013(2) 0.650(2) 0.061(4) Uani d PDU 0.504(6) A 2 C
H3D1 0.8474 0.0261 0.5375 0.073 Uiso calc PR 0.504(6) A 2 H
H3D2 0.8311 -0.0617 0.6712 0.073 Uiso calc PR 0.504(6) A 2 H
C4D 0.9525(12) 0.000(2) 0.7210(18) 0.061(4) Uani d PDU 0.504(6) A 2 C
H4D1 0.9701 -0.0861 0.7136 0.073 Uiso calc PR 0.504(6) A 2 H
H4D2 0.9824 0.0553 0.6673 0.073 Uiso calc PR 0.504(6) A 2 H
C5D 0.9649(4) 0.0391(7) 0.8890(7) 0.0546(19) Uani d PDU 0.504(6) . 2 C
C6D 0.7509(13) 0.126(5) 0.765(3) 0.072(3) Uani d PDU 0.504(6) A 2 C
H6D1 0.7478 0.0546 0.8319 0.087 Uiso calc PR 0.504(6) A 2 H
H6D2 0.7433 0.2025 0.8206 0.087 Uiso calc PR 0.504(6) A 2 H
C7D 0.6841(16) 0.117(3) 0.618(3) 0.067(4) Uani d PDU 0.504(6) A 2 C
C8D 0.6576(16) 0.000(3) 0.554(3) 0.079(5) Uani d PDU 0.504(6) A 2 C
H8D 0.6818 -0.0724 0.6041 0.095 Uiso calc PR 0.504(6) A 2 H
C9D 0.5959(14) -0.011(2) 0.418(3) 0.081(5) Uani d PDU 0.504(6) A 2 C
H9D 0.5785 -0.0897 0.3760 0.097 Uiso calc PR 0.504(6) A 2 H
C10D 0.561(2) 0.098(3) 0.347(4) 0.087(4) Uani d PDU 0.504(6) A 2 C
C11D 0.5862(14) 0.216(2) 0.408(3) 0.073(5) Uani d PDU 0.504(6) A 2 C
H11D 0.5611 0.2890 0.3592 0.087 Uiso calc PR 0.504(6) A 2 H
C12D 0.6486(14) 0.224(3) 0.541(3) 0.065(4) Uani d PDU 0.504(6) A 2 C
H12D 0.6674 0.3029 0.5798 0.078 Uiso calc PR 0.504(6) A 2 H
Cl1D 0.4827(10) 0.095(2) 0.1795(18) 0.164(6) Uani d PDU 0.504(6) A 2 Cl
C13D 1.0478(4) 0.0706(6) 1.0003(7) 0.0501(19) Uani d PDU 0.504(6) . 2 C
H13D 1.0411 0.1501 1.0530 0.060 Uiso calc PR 0.504(6) A 2 H
C14D 1.1238(5) 0.0821(9) 0.9474(10) 0.061(2) Uani d PDU 0.504(6) A 2 C
C15D 1.1781(8) 0.1779(14) 1.0130(19) 0.074(4) Uani d PDU 0.504(6) A 2 C
H15D 1.1641 0.2346 1.0825 0.089 Uiso calc PR 0.504(6) A 2 H
C16D 1.2517(10) 0.1904(16) 0.9771(19) 0.084(5) Uani d PDU 0.504(6) A 2 C
H16D 1.2866 0.2555 1.0224 0.101 Uiso calc PR 0.504(6) A 2 H
C17D 1.2751(7) 0.1083(16) 0.875(2) 0.086(3) Uani d PDU 0.504(6) A 2 C
H17D 1.3261 0.1144 0.8543 0.103 Uiso calc PR 0.504(6) A 2 H
C18D 1.2195(11) 0.016(2) 0.805(3) 0.080(4) Uani d PDU 0.504(6) A 2 C
H18D 1.2324 -0.0376 0.7307 0.096 Uiso calc PR 0.504(6) A 2 H
C19D 1.1459(6) 0.0010(10) 0.8419(11) 0.063(2) Uani d PDU 0.504(6) A 2 C
H19D 1.1109 -0.0638 0.7959 0.076 Uiso calc PR 0.504(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 C5M . 127.1(12)
O1M C1M C2M . 123.7(13)
C5M C1M C2M . 108.5(11)
C6M C2M C1M . 113.3(17)
C6M C2M C3M . 118(2)
C1M C2M C3M . 104.0(12)
C2M C3M C4M . 103.0(14)
C5M C4M C3M . 106.4(12)
C13M C5M C1M . 121.0(9)
C13M C5M C4M . 132.7(9)
C1M C5M C4M . 105.9(11)
C7M C6M C2M . 112.9(18)
C8M C7M C12M . 117.2(16)
C8M C7M C6M . 121.4(19)
C12M C7M C6M . 121.4(19)
C7M C8M C9M . 122.3(18)
C10M C9M C8M . 119.7(18)
C9M C10M C11M . 119.1(15)
C9M C10M Cl1M . 120.8(17)
C11M C10M Cl1M . 120.1(17)
C12M C11M C10M . 120.6(18)
C11M C12M C7M . 121.1(18)
C5M C13M C14M . 130.9(7)
C15M C14M C19M . 116.7(9)
C15M C14M C13M . 117.6(9)
C19M C14M C13M . 125.5(8)
C14M C15M C16M . 121.1(13)
C15M C16M C17M . 122.2(14)
C16M C17M C18M . 117.3(12)
C19M C18M C17M . 119.9(15)
C18M C19M C14M . 122.7(12)
O1D C1D C5D . 125.9(13)
O1D C1D C2D . 122.8(14)
C5D C1D C2D . 110.1(12)
C6D C2D C1D . 113.6(18)
C6D C2D C3D . 117(2)
C1D C2D C3D . 103.8(13)
C2D C3D C4D . 104.7(12)
C5D C4D C3D . 104.5(11)
C4D C5D C1D . 102.7(10)
C4D C5D C13D . 124.7(9)
C1D C5D C13D . 112.4(8)
C4D C5D C13D 3_757 113.8(11)
C1D C5D C13D 3_757 112.7(8)
C13D C5D C13D 3_757 90.6(5)
C7D C6D C2D . 112.1(19)
C8D C7D C12D . 118.4(15)
C8D C7D C6D . 120.8(19)
C12D C7D C6D . 120.8(19)
C7D C8D C9D . 121.8(17)
C10D C9D C8D . 117.8(17)
C9D C10D C11D . 121.7(15)
C9D C10D Cl1D . 121.6(17)
C11D C10D Cl1D . 116.6(17)
C12D C11D C10D . 118.9(17)
C11D C12D C7D . 121.3(17)
C14D C13D C5D . 123.1(6)
C14D C13D C5D 3_757 121.6(6)
C5D C13D C5D 3_757 89.4(5)
C19D C14D C15D . 117.8(10)
C19D C14D C13D . 124.4(8)
C15D C14D C13D . 117.8(9)
C16D C15D C14D . 121.4(15)
C15D C16D C17D . 121.2(15)
C16D C17D C18D . 117.3(12)
C19D C18D C17D . 121.9(14)
C18D C19D C14D . 120.3(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1M C1M . 1.226(18)
C1M C5M . 1.509(13)
C1M C2M . 1.524(15)
C2M C6M . 1.518(15)
C2M C3M . 1.530(16)
C3M C4M . 1.554(16)
C4M C5M . 1.518(15)
C5M C13M . 1.321(9)
C6M C7M . 1.487(14)
C7M C8M . 1.379(15)
C7M C12M . 1.387(15)
C8M C9M . 1.380(15)
C9M C10M . 1.376(16)
C10M C11M . 1.382(16)
C10M Cl1M . 1.726(14)
C11M C12M . 1.378(15)
C13M C14M . 1.455(10)
C14M C15M . 1.374(13)
C14M C19M . 1.387(12)
C15M C16M . 1.378(14)
C16M C17M . 1.379(16)
C17M C18M . 1.389(16)
C18M C19M . 1.380(15)
O1D C1D . 1.224(18)
C1D C5D . 1.505(14)
C1D C2D . 1.525(15)
C2D C6D . 1.520(16)
C2D C3D . 1.534(15)
C3D C4D . 1.549(15)
C4D C5D . 1.497(13)
C5D C13D . 1.535(8)
C5D C13D 3_757 1.566(9)
C6D C7D . 1.494(15)
C7D C8D . 1.378(15)
C7D C12D . 1.381(15)
C8D C9D . 1.385(15)
C9D C10D . 1.376(16)
C10D C11D . 1.380(16)
C10D Cl1D . 1.717(14)
C11D C12D . 1.370(15)
C13D C14D . 1.481(10)
C13D C5D 3_757 1.566(9)
C14D C19D . 1.384(11)
C14D C15D . 1.394(14)
C15D C16D . 1.369(14)
C16D C17D . 1.377(15)
C17D C18D . 1.393(16)
C18D C19D . 1.375(13)
