#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/39/2103941.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_2103941
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                 104.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.089(5)
_cell_length_b                   10.564(3)
_cell_length_c                   8.812(3)
_cell_measurement_reflns_used    653
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      5
_cell_volume                     1536.9(8)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_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            7423
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         5.59
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.9642
_exptl_absorpt_correction_T_min  0.8513
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.283
_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         0.117
_refine_diff_density_min         -0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0747
_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)+(0.0530P)²+0.3360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1768
_reflns_number_gt                1746
_reflns_number_total             2955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk0133.cif
_cod_data_source_block           32D
_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:

'_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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.3360P] 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^)+(0.0530P)^2^+0.3360P] 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               2103941
_cod_database_fobs_code          2103941
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 0.9058(9) 0.2411(15) 0.951(2) 0.095(4) Uani d PDU 0.680(5) A 1 O
C1M 0.9137(6) 0.1682(10) 0.8473(10) 0.061(2) Uani d PDU 0.680(5) A 1 C
C2M 0.8432(6) 0.1158(12) 0.7228(16) 0.054(2) Uani d PDU 0.680(5) A 1 C
H2M 0.8380 0.1699 0.6305 0.065 Uiso calc PR 0.680(5) A 1 H
C3M 0.8750(6) -0.0086(8) 0.6821(10) 0.058(2) Uani d PDU 0.680(5) A 1 C
H3M1 0.8487 -0.0324 0.5748 0.070 Uiso calc PR 0.680(5) A 1 H
H3M2 0.8662 -0.0749 0.7521 0.070 Uiso calc PR 0.680(5) A 1 H
C4M 0.9665(6) 0.0134(13) 0.7025(11) 0.060(2) Uani d PDU 0.680(5) A 1 C
H4M1 0.9966 -0.0643 0.7342 0.072 Uiso calc PR 0.680(5) A 1 H
H4M2 0.9766 0.0426 0.6050 0.072 Uiso calc PR 0.680(5) A 1 H
C5M 0.9910(3) 0.1125(4) 0.8281(4) 0.0517(11) Uani d PDU 0.680(5) A 1 C
C6M 0.7621(7) 0.121(2) 0.7608(18) 0.074(3) Uani d PDU 0.680(5) A 1 C
H6M1 0.7593 0.0534 0.8337 0.089 Uiso calc PR 0.680(5) A 1 H
H6M2 0.7576 0.2008 0.8125 0.089 Uiso calc PR 0.680(5) A 1 H
C7M 0.6919(9) 0.1088(14) 0.619(2) 0.063(3) Uani d PDU 0.680(5) A 1 C
C8M 0.6511(8) -0.0043(14) 0.5816(17) 0.079(3) Uani d PDU 0.680(5) A 1 C
H8M 0.6679 -0.0740 0.6463 0.094 Uiso calc PR 0.680(5) A 1 H
C9M 0.5868(5) -0.0173(11) 0.4528(12) 0.076(2) Uani d PDU 0.680(5) A 1 C
H9M 0.5619 -0.0957 0.4281 0.092 Uiso calc PR 0.680(5) A 1 H
C10M 0.5595(7) 0.0852(14) 0.3612(15) 0.078(3) Uani d PDU 0.680(5) A 1 C
C11M 0.5994(12) 0.1996(14) 0.393(2) 0.083(3) Uani d PDU 0.680(5) A 1 C
H11M 0.5828 0.2685 0.3271 0.099 Uiso calc PR 0.680(5) A 1 H
C12M 0.6644(7) 0.2109(13) 0.5237(14) 0.068(3) Uani d PDU 0.680(5) A 1 C
H12M 0.6898 0.2890 0.5475 0.082 Uiso calc PR 0.680(5) A 1 H
Cl1M 0.4862(5) 0.0661(10) 0.1866(8) 0.1190(14) Uani d PDU 0.680(5) A 1 Cl
C13M 1.0626(3) 0.1574(4) 0.9068(5) 0.0574(12) Uani d PDU 0.680(5) A 1 C
H13M 1.0604 0.2186 0.9815 0.069 Uiso calc PR 0.680(5) A 1 H
C14M 1.1441(3) 0.1268(5) 0.8955(6) 0.0528(12) Uani d PDU 0.680(5) A 1 C
C15M 1.2088(5) 0.1895(6) 0.9945(7) 0.0593(19) Uani d PDU 0.680(5) A 1 C
H15M 1.1994 0.2465 1.0682 0.071 Uiso calc PR 0.680(5) A 1 H
C16M 1.2876(5) 0.1679(7) 0.9844(11) 0.078(2) Uani d PDU 0.680(5) A 1 C
H16M 1.3300 0.2117 1.0511 0.094 Uiso calc PR 0.680(5) A 1 H
C17M 1.3041(4) 0.0845(10) 0.8793(12) 0.085(2) Uani d PDU 0.680(5) A 1 C
H17M 1.3572 0.0700 0.8753 0.101 Uiso calc PR 0.680(5) A 1 H
C18M 1.2412(6) 0.0224(12) 0.7797(13) 0.076(2) Uani d PDU 0.680(5) A 1 C
H18M 1.2516 -0.0333 0.7055 0.092 Uiso calc PR 0.680(5) A 1 H
C19M 1.1618(4) 0.0415(6) 0.7882(7) 0.0676(15) Uani d PDU 0.680(5) A 1 C
H19M 1.1200 -0.0033 0.7213 0.081 Uiso calc PR 0.680(5) A 1 H
O1D 0.9221(19) 0.244(3) 0.967(4) 0.088(6) Uani d PDU 0.320(5) A 2 O
C1D 0.9068(12) 0.1486(19) 0.885(2) 0.057(4) Uani d PDU 0.320(5) A 2 C
C2D 0.8397(14) 0.143(3) 0.732(3) 0.055(4) Uani d PDU 0.320(5) A 2 C
H2D 0.8414 0.2183 0.6682 0.066 Uiso calc PR 0.320(5) A 2 H
C3D 0.8599(13) 0.0235(18) 0.649(2) 0.054(4) Uani d PDU 0.320(5) A 2 C
H3D1 0.8487 0.0372 0.5371 0.065 Uiso calc PR 0.320(5) A 2 H
H3D2 0.8282 -0.0480 0.6687 0.065 Uiso calc PR 0.320(5) A 2 H
C4D 0.9514(13) 0.000(3) 0.721(2) 0.054(4) Uani d PDU 0.320(5) A 2 C
H4D1 0.9644 -0.0894 0.7150 0.064 Uiso calc PR 0.320(5) A 2 H
H4D2 0.9839 0.0488 0.6671 0.064 Uiso calc PR 0.320(5) A 2 H
C5D 0.9654(5) 0.0413(8) 0.8886(9) 0.055(2) Uani d PDU 0.320(5) . 2 C
C6D 0.7581(15) 0.135(5) 0.774(4) 0.067(4) Uani d PDU 0.320(5) A 2 C
H6D1 0.7587 0.0619 0.8412 0.080 Uiso calc PR 0.320(5) A 2 H
H6D2 0.7510 0.2098 0.8320 0.080 Uiso calc PR 0.320(5) A 2 H
C7D 0.6889(19) 0.123(3) 0.634(4) 0.060(4) Uani d PDU 0.320(5) A 2 C
C8D 0.6652(17) 0.006(3) 0.567(3) 0.077(5) Uani d PDU 0.320(5) A 2 C
H8D 0.6885 -0.0661 0.6196 0.092 Uiso calc PR 0.320(5) A 2 H
C9D 0.6083(11) -0.007(2) 0.425(3) 0.071(4) Uani d PDU 0.320(5) A 2 C
H9D 0.5929 -0.0870 0.3852 0.085 Uiso calc PR 0.320(5) A 2 H
C10D 0.5740(15) 0.099(3) 0.342(3) 0.067(4) Uani d PDU 0.320(5) A 2 C
C11D 0.595(3) 0.217(3) 0.411(4) 0.078(5) Uani d PDU 0.320(5) A 2 C
H11D 0.5698 0.2896 0.3605 0.094 Uiso calc PR 0.320(5) A 2 H
C12D 0.6510(16) 0.227(3) 0.553(3) 0.062(4) Uani d PDU 0.320(5) A 2 C
H12D 0.6642 0.3073 0.5959 0.074 Uiso calc PR 0.320(5) A 2 H
Cl1D 0.4898(12) 0.098(2) 0.187(2) 0.161(7) Uani d PDU 0.320(5) A 2 Cl
C13D 1.0483(5) 0.0696(7) 1.0008(8) 0.053(2) Uani d PDU 0.320(5) . 2 C
H13D 1.0424 0.1489 1.0546 0.063 Uiso calc PR 0.320(5) A 2 H
C14D 1.1221(6) 0.0824(10) 0.9460(11) 0.056(3) Uani d PDU 0.320(5) A 2 C
C15D 1.1763(8) 0.1768(15) 1.0140(18) 0.069(4) Uani d PDU 0.320(5) A 2 C
H15D 1.1624 0.2329 1.0841 0.083 Uiso calc PR 0.320(5) A 2 H
C16D 1.2509(10) 0.1896(13) 0.9800(17) 0.065(4) Uani d PDU 0.320(5) A 2 C
H16D 1.2858 0.2544 1.0260 0.078 Uiso calc PR 0.320(5) A 2 H
C17D 1.2730(9) 0.107(2) 0.878(2) 0.082(4) Uani d PDU 0.320(5) A 2 C
H17D 1.3235 0.1127 0.8570 0.098 Uiso calc PR 0.320(5) A 2 H
C18D 1.2186(13) 0.013(2) 0.808(3) 0.072(4) Uani d PDU 0.320(5) A 2 C
H18D 1.2319 -0.0413 0.7355 0.086 Uiso calc PR 0.320(5) A 2 H
C19D 1.1454(8) 0.0006(12) 0.8427(13) 0.065(3) Uani d PDU 0.320(5) A 2 C
H19D 1.1106 -0.0642 0.7962 0.077 Uiso calc PR 0.320(5) 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 . 127.0(8)
O1M C1M C2M . 123.3(9)
C5M C1M C2M . 109.7(7)
C3M C2M C6M . 119.7(12)
C3M C2M C1M . 102.9(7)
C6M C2M C1M . 115.6(9)
C2M C3M C4M . 105.0(8)
C5M C4M C3M . 105.7(7)
C13M C5M C1M . 121.5(5)
C13M C5M C4M . 132.6(5)
C1M C5M C4M . 105.8(6)
C7M C6M C2M . 113.2(11)
C12M C7M C8M . 117.7(10)
C12M C7M C6M . 121.1(12)
C8M C7M C6M . 121.2(12)
C9M C8M C7M . 122.1(11)
C10M C9M C8M . 119.4(9)
C9M C10M C11M . 120.1(9)
C9M C10M Cl1M . 119.7(10)
C11M C10M Cl1M . 119.3(10)
C10M C11M C12M . 119.6(11)
C7M C12M C11M . 121.0(11)
C5M C13M C14M . 130.7(4)
C15M C14M C19M . 117.3(5)
C15M C14M C13M . 118.1(5)
C19M C14M C13M . 124.6(5)
C14M C15M C16M . 120.6(7)
C17M C16M C15M . 121.7(7)
C16M C17M C18M . 118.7(7)
C17M C18M C19M . 120.8(8)
C18M C19M C14M . 121.0(7)
O1D C1D C5D . 124.4(15)
O1D C1D C2D . 123.2(17)
C5D C1D C2D . 109.4(14)
C1D C2D C6D . 108(2)
C1D C2D C3D . 103.9(15)
C6D C2D C3D . 113(2)
C2D C3D C4D . 105.5(15)
C5D C4D C3D . 103.9(12)
C4D C5D C1D . 105.4(12)
C4D C5D C13D . 125.3(10)
C1D C5D C13D . 111.4(10)
C4D C5D C13D 3_757 112.2(12)
C1D C5D C13D 3_757 111.5(10)
C13D C5D C13D 3_757 90.4(6)
C7D C6D C2D . 113(2)
C12D C7D C8D . 116.5(19)
C12D C7D C6D . 122(2)
C8D C7D C6D . 121(2)
C9D C8D C7D . 122(2)
C8D C9D C10D . 120.2(18)
C9D C10D C11D . 117.9(18)
C9D C10D Cl1D . 125.0(19)
C11D C10D Cl1D . 114.8(19)
C12D C11D C10D . 120(2)
C11D C12D C7D . 122(2)
C14D C13D C5D . 122.4(7)
C14D C13D C5D 3_757 123.2(7)
C5D C13D C5D 3_757 89.6(6)
C19D C14D C15D . 117.3(10)
C19D C14D C13D . 125.1(9)
C15D C14D C13D . 117.3(10)
C14D C15D C16D . 121.7(15)
C17D C16D C15D . 120.0(14)
C16D C17D C18D . 118.6(13)
C19D C18D C17D . 121.0(15)
C18D C19D C14D . 121.4(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1M C1M . 1.230(12)
C1M C5M . 1.494(9)
C1M C2M . 1.510(10)
C2M C3M . 1.501(9)
C2M C6M . 1.508(10)
C3M C4M . 1.544(10)
C4M C5M . 1.502(10)
C5M C13M . 1.330(5)
C6M C7M . 1.500(10)
C7M C12M . 1.371(10)
C7M C8M . 1.380(10)
C8M C9M . 1.368(10)
C9M C10M . 1.359(10)
C10M C11M . 1.380(12)
C10M Cl1M . 1.726(9)
C11M C12M . 1.382(10)
C13M C14M . 1.458(6)
C14M C15M . 1.387(8)
C14M C19M . 1.394(7)
C15M C16M . 1.391(7)
C16M C17M . 1.360(10)
C17M C18M . 1.367(11)
C18M C19M . 1.393(10)
O1D C1D . 1.224(19)
C1D C5D . 1.508(16)
C1D C2D . 1.528(18)
C2D C6D . 1.532(19)
C2D C3D . 1.541(18)
C3D C4D . 1.549(17)
C4D C5D . 1.500(15)
C5D C13D . 1.533(10)
C5D C13D 3_757 1.580(11)
C6D C7D . 1.478(17)
C7D C12D . 1.378(18)
C7D C8D . 1.382(18)
C8D C9D . 1.378(18)
C9D C10D . 1.381(17)
C10D C11D . 1.392(18)
C10D Cl1D . 1.711(17)
C11D C12D . 1.372(18)
C13D C14D . 1.467(11)
C13D C5D 3_757 1.580(11)
C14D C19D . 1.386(13)
C14D C15D . 1.388(15)
C15D C16D . 1.389(12)
C16D C17D . 1.377(17)
C17D C18D . 1.386(18)
C18D C19D . 1.370(15)
