#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/39/2103944.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_2103944
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                 104.07(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.781(7)
_cell_length_b                   10.627(5)
_cell_length_c                   8.735(4)
_cell_measurement_reflns_used    846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      5
_cell_volume                     1511.0(12)
_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  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0624
_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            7399
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         5.60
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9636
_exptl_absorpt_correction_T_min  0.8491
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.305
_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         -0.130
_refine_ls_extinction_coef       0.042(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0868
_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)+(0.0579P)²+0.8067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.2078
_reflns_number_gt                1788
_reflns_number_total             2920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk0133.cif
_cod_data_source_block           78D
_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^)+(0.0579P)^2^+0.8067P] 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^)+(0.0579P)^2^+0.8067P] 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               2103944
_cod_database_fobs_code          2103944
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 0.893(2) 0.224(7) 0.953(7) 0.065(7) Uani d PDU 0.219(6) A 1 O
C1M 0.9052(13) 0.165(3) 0.840(4) 0.053(5) Uani d PDU 0.219(6) A 1 C
C2M 0.8383(15) 0.105(4) 0.709(5) 0.055(5) Uani d PDU 0.219(6) A 1 C
H2M 0.8281 0.1600 0.6159 0.066 Uiso calc PR 0.219(6) A 1 H
C3M 0.8740(18) -0.020(3) 0.668(5) 0.060(5) Uani d PDU 0.219(6) A 1 C
H3M1 0.8509 -0.0423 0.5581 0.072 Uiso calc PR 0.219(6) A 1 H
H3M2 0.8632 -0.0875 0.7345 0.072 Uiso calc PR 0.219(6) A 1 H
C4M 0.9674(19) 0.006(5) 0.698(6) 0.055(5) Uani d PDU 0.219(6) A 1 C
H4M1 0.9986 -0.0698 0.7337 0.066 Uiso calc PR 0.219(6) A 1 H
H4M2 0.9811 0.0353 0.6025 0.066 Uiso calc PR 0.219(6) A 1 H
C5M 0.9873(8) 0.1081(15) 0.8266(16) 0.052(4) Uani d PDU 0.219(6) A 1 C
C6M 0.7587(17) 0.093(4) 0.763(4) 0.065(6) Uani d PDU 0.219(6) A 1 C
H6M1 0.7607 0.0181 0.8278 0.079 Uiso calc PR 0.219(6) A 1 H
H6M2 0.7517 0.1655 0.8259 0.079 Uiso calc PR 0.219(6) A 1 H
C7M 0.6901(19) 0.084(3) 0.623(5) 0.052(5) Uani d PDU 0.219(6) A 1 C
C8M 0.652(3) -0.028(3) 0.569(6) 0.077(6) Uani d PDU 0.219(6) A 1 C
H8M 0.6713 -0.1029 0.6205 0.092 Uiso calc PR 0.219(6) A 1 H
C9M 0.586(4) -0.030(4) 0.439(7) 0.089(6) Uani d PDU 0.219(6) A 1 C
H9M 0.5610 -0.1064 0.4033 0.107 Uiso calc PR 0.219(6) A 1 H
C10M 0.556(4) 0.080(4) 0.361(6) 0.077(6) Uani d PDU 0.219(6) A 1 C
C11M 0.593(3) 0.194(4) 0.416(6) 0.079(6) Uani d PDU 0.219(6) A 1 C
H11M 0.5714 0.2689 0.3697 0.095 Uiso calc PR 0.219(6) A 1 H
C12M 0.662(3) 0.194(3) 0.541(5) 0.069(6) Uani d PDU 0.219(6) A 1 C
H12M 0.6905 0.2689 0.5697 0.082 Uiso calc PR 0.219(6) A 1 H
Cl1M 0.491(2) 0.070(5) 0.178(5) 0.130(7) Uani d PDU 0.219(6) A 1 Cl
C13M 1.0580(8) 0.1528(14) 0.9035(17) 0.058(4) Uani d PDU 0.219(6) A 1 C
H13M 1.0545 0.2159 0.9753 0.070 Uiso calc PR 0.219(6) A 1 H
C14M 1.1410(9) 0.1215(17) 0.897(2) 0.057(4) Uani d PDU 0.219(6) A 1 C
C15M 1.2054(15) 0.185(3) 0.998(4) 0.071(6) Uani d PDU 0.219(6) A 1 C
H15M 1.1934 0.2392 1.0731 0.085 Uiso calc PR 0.219(6) A 1 H
C16M 1.2861(16) 0.171(4) 0.992(5) 0.093(6) Uani d PDU 0.219(6) A 1 C
H16M 1.3270 0.2162 1.0609 0.111 Uiso calc PR 0.219(6) A 1 H
C17M 1.3067(14) 0.089(4) 0.884(5) 0.096(6) Uani d PDU 0.219(6) A 1 C
H17M 1.3612 0.0742 0.8834 0.115 Uiso calc PR 0.219(6) A 1 H
C18M 1.2427(16) 0.031(3) 0.776(4) 0.074(5) Uani d PDU 0.219(6) A 1 C
H18M 1.2544 -0.0158 0.6941 0.089 Uiso calc PR 0.219(6) A 1 H
C19M 1.1621(14) 0.040(2) 0.788(2) 0.066(4) Uani d PDU 0.219(6) A 1 C
H19M 1.1216 -0.0078 0.7220 0.080 Uiso calc PR 0.219(6) A 1 H
O1D 0.9093(7) 0.235(2) 0.958(2) 0.078(3) Uani d PDU 0.781(6) A 2 O
C1D 0.9024(4) 0.1419(7) 0.8729(10) 0.055(2) Uani d PDU 0.781(6) A 2 C
C2D 0.8342(5) 0.1252(11) 0.7260(14) 0.0560(19) Uani d PDU 0.781(6) A 2 C
H2D 0.8375 0.1956 0.6554 0.067 Uiso calc PR 0.781(6) A 2 H
C3D 0.8598(5) 0.0062(9) 0.6513(14) 0.060(2) Uani d PDU 0.781(6) A 2 C
H3D1 0.8333 -0.0676 0.6817 0.072 Uiso calc PR 0.781(6) A 2 H
H3D2 0.8456 0.0126 0.5371 0.072 Uiso calc PR 0.781(6) A 2 H
C4D 0.9531(5) -0.0007(13) 0.7159(14) 0.058(2) Uani d PDU 0.781(6) A 2 C
H4D1 0.9732 -0.0854 0.7080 0.070 Uiso calc PR 0.781(6) A 2 H
H4D2 0.9810 0.0565 0.6597 0.070 Uiso calc PR 0.781(6) A 2 H
C5D 0.9653(3) 0.0385(4) 0.8862(5) 0.0488(12) Uani d PDU 0.781(6) . 2 C
C6D 0.7480(5) 0.1272(9) 0.7559(12) 0.064(2) Uani d PDU 0.781(6) A 2 C
H6D1 0.7431 0.0574 0.8245 0.077 Uiso calc PR 0.781(6) A 2 H
H6D2 0.7416 0.2043 0.8111 0.077 Uiso calc PR 0.781(6) A 2 H
C7D 0.6806(6) 0.1190(7) 0.6115(13) 0.057(2) Uani d PDU 0.781(6) A 2 C
C8D 0.6459(8) 0.0065(7) 0.5558(16) 0.078(2) Uani d PDU 0.781(6) A 2 C
H8D 0.6648 -0.0662 0.6121 0.093 Uiso calc PR 0.781(6) A 2 H
C9D 0.5844(11) -0.0040(11) 0.4209(19) 0.091(3) Uani d PDU 0.781(6) A 2 C
H9D 0.5626 -0.0825 0.3870 0.109 Uiso calc PR 0.781(6) A 2 H
C10D 0.5552(11) 0.1018(12) 0.3361(16) 0.079(2) Uani d PDU 0.781(6) A 2 C
C11D 0.5869(9) 0.2164(11) 0.3881(15) 0.078(2) Uani d PDU 0.781(6) A 2 C
H11D 0.5673 0.2888 0.3316 0.094 Uiso calc PR 0.781(6) A 2 H
C12D 0.6483(7) 0.2243(8) 0.5250(14) 0.070(2) Uani d PDU 0.781(6) A 2 C
H12D 0.6687 0.3032 0.5605 0.084 Uiso calc PR 0.781(6) A 2 H
Cl1D 0.4741(7) 0.0924(15) 0.1727(14) 0.133(3) Uani d PDU 0.781(6) A 2 Cl
C13D 1.0481(2) 0.0718(4) 1.0010(4) 0.0493(12) Uani d PDU 0.781(6) . 2 C
H13D 1.0406 0.1514 1.0525 0.059 Uiso calc PR 0.781(6) A 2 H
C14D 1.1257(3) 0.0823(5) 0.9472(6) 0.0561(14) Uani d PDU 0.781(6) A 2 C
C15D 1.1804(5) 0.1774(9) 1.0124(10) 0.072(2) Uani d PDU 0.781(6) A 2 C
H15D 1.1656 0.2349 1.0810 0.087 Uiso calc PR 0.781(6) A 2 H
C16D 1.2557(6) 0.1884(11) 0.9778(12) 0.096(3) Uani d PDU 0.781(6) A 2 C
H16D 1.2912 0.2525 1.0236 0.115 Uiso calc PR 0.781(6) A 2 H
C17D 1.2786(5) 0.1061(11) 0.8770(13) 0.097(3) Uani d PDU 0.781(6) A 2 C
H17D 1.3300 0.1134 0.8554 0.116 Uiso calc PR 0.781(6) A 2 H
C18D 1.2259(5) 0.0124(9) 0.8071(10) 0.077(2) Uani d PDU 0.781(6) A 2 C
H18D 1.2409 -0.0430 0.7366 0.092 Uiso calc PR 0.781(6) A 2 H
C19D 1.1498(4) 0.0008(6) 0.8426(7) 0.0647(15) Uani d PDU 0.781(6) A 2 C
H19D 1.1143 -0.0629 0.7952 0.078 Uiso calc PR 0.781(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 . 125.3(18)
O1M C1M C5M . 126.3(19)
C2M C1M C5M . 106.4(15)
C6M C2M C1M . 110(2)
C6M C2M C3M . 115(3)
C1M C2M C3M . 106.3(19)
C2M C3M C4M . 103.9(19)
C5M C4M C3M . 106.4(17)
C13M C5M C4M . 129.9(15)
C13M C5M C1M . 122.5(14)
C4M C5M C1M . 107.3(15)
C7M C6M C2M . 108(2)
C8M C7M C12M . 119(2)
C8M C7M C6M . 123(2)
C12M C7M C6M . 118(2)
C7M C8M C9M . 120(2)
C8M C9M C10M . 121(2)
C11M C10M C9M . 119(2)
C11M C10M Cl1M . 121(2)
C9M C10M Cl1M . 118(2)
C10M C11M C12M . 120(2)
C11M C12M C7M . 121(2)
C5M C13M C14M . 131.3(14)
C19M C14M C15M . 116.6(16)
C19M C14M C13M . 125.3(15)
C15M C14M C13M . 117.9(17)
C16M C15M C14M . 123(2)
C15M C16M C17M . 120(2)
C16M C17M C18M . 117(2)
C19M C18M C17M . 122(2)
C18M C19M C14M . 120.7(19)
O1D C1D C5D . 125.5(7)
O1D C1D C2D . 123.4(9)
C5D C1D C2D . 110.6(6)
C1D C2D C6D . 114.0(7)
C1D C2D C3D . 103.1(6)
C6D C2D C3D . 117.3(7)
C4D C3D C2D . 104.5(6)
C5D C4D C3D . 103.4(6)
C1D C5D C4D . 101.5(6)
C1D C5D C13D . 112.6(4)
C4D C5D C13D . 126.1(5)
C1D C5D C13D 3_757 112.6(4)
C4D C5D C13D 3_757 113.8(7)
C13D C5D C13D 3_757 90.4(3)
C7D C6D C2D . 114.3(7)
C8D C7D C12D . 115.8(7)
C8D C7D C6D . 121.8(7)
C12D C7D C6D . 122.3(7)
C7D C8D C9D . 123.0(7)
C8D C9D C10D . 119.6(8)
C11D C10D C9D . 119.6(8)
C11D C10D Cl1D . 119.7(8)
C9D C10D Cl1D . 120.6(8)
C10D C11D C12D . 119.5(8)
C11D C12D C7D . 122.4(8)
C14D C13D C5D . 121.9(4)
C14D C13D C5D 3_757 121.3(4)
C5D C13D C5D 3_757 89.6(3)
C19D C14D C15D . 117.0(6)
C19D C14D C13D . 125.2(5)
C15D C14D C13D . 117.7(5)
C16D C15D C14D . 121.4(8)
C17D C16D C15D . 120.5(8)
C16D C17D C18D . 120.0(8)
C17D C18D C19D . 119.5(7)
C14D C19D C18D . 121.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1M C1M . 1.22(2)
C1M C2M . 1.537(19)
C1M C5M . 1.537(17)
C2M C6M . 1.53(2)
C2M C3M . 1.54(2)
C3M C4M . 1.551(19)
C4M C5M . 1.537(18)
C5M C13M . 1.303(14)
C6M C7M . 1.468(18)
C7M C8M . 1.380(18)
C7M C12M . 1.391(18)
C8M C9M . 1.384(19)
C9M C10M . 1.388(19)
C10M C11M . 1.383(19)
C10M Cl1M . 1.705(19)
C11M C12M . 1.384(19)
C13M C14M . 1.448(15)
C14M C19M . 1.391(17)
C14M C15M . 1.394(18)
C15M C16M . 1.376(18)
C16M C17M . 1.386(19)
C17M C18M . 1.390(19)
C18M C19M . 1.385(18)
O1D C1D . 1.224(12)
C1D C5D . 1.508(8)
C1D C2D . 1.509(9)
C2D C6D . 1.531(8)
C2D C3D . 1.532(8)
C3D C4D . 1.531(9)
C4D C5D . 1.510(10)
C5D C13D . 1.544(6)
C5D C13D 3_757 1.582(6)
C6D C7D . 1.478(8)
C7D C8D . 1.366(8)
C7D C12D . 1.385(8)
C8D C9D . 1.369(9)
C9D C10D . 1.370(9)
C10D C11D . 1.363(9)
C10D Cl1D . 1.718(9)
C11D C12D . 1.378(9)
C13D C14D . 1.493(7)
C13D C5D 3_757 1.582(6)
C14D C19D . 1.389(7)
C14D C15D . 1.390(8)
C15D C16D . 1.374(9)
C16D C17D . 1.362(10)
C17D C18D . 1.373(10)
C18D C19D . 1.390(8)
