#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103825.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_2103825
loop_
_publ_author_name
'Ohba, Shigeru'
'Ito, Yoshikatsu'
_publ_section_title
;
 Single-crystal-to-single-crystal photodimerization of
 4-chlorocinnamoyl-O,O'-dimethyldopamine
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              149
_journal_page_last               155
_journal_paper_doi               10.1107/S0108768102022760
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C19 H20 Cl N O3 '
_chemical_formula_sum            'C19 H20 Cl N O3'
_chemical_formula_weight         345.82
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 91.292(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.195(3)
_cell_length_b                   4.9784(11)
_cell_length_c                   33.646(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      11.8
_cell_measurement_theta_min      10.1
_cell_volume                     3549.3(10)
_computing_cell_refinement
' WinAFC Diffractometer Control Software (Rigaku, 1999)'
_computing_data_collection
' WinAFC Diffractometer Control Software (Rigaku, 1999)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 2001)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            5116
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        1.70
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456.0
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4096
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0727P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1945
_reflns_number_gt                1066
_reflns_number_total             4096
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm0063.cif
_cod_data_source_block           Ie
_cod_original_formula_sum        'C19 H20 Cl N O3 '
_cod_database_code               2103825
_cod_database_fobs_code          2103825
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
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_type_symbol
Cl 0.4112(4) 0.466(2) 0.1899(2) 0.183(3) Uani d P 0.72 Cl
Cl* 0.4287(9) 0.429(4) 0.1977(3) 0.132(5) Uani d P 0.28 Cl
O2 0.6232(2) 0.8837(6) -0.01696(8) 0.1280(10) Uani d . 1.00 O
O3 0.7839(2) 0.0637(7) -0.20335(9) 0.1151(9) Uani d . 1.00 O
O4 0.87290(10) 0.4107(6) -0.21051(8) 0.1210(10) Uani d . 1.00 O
N5 0.6572(2) 0.4636(6) -0.02611(8) 0.0909(10) Uani d . 1.00 N
C6 0.4475(5) 0.544(2) 0.1474(4) 0.105(4) Uani d P 0.72 C
C6* 0.4620(10) 0.461(5) 0.1504(6) 0.0607 Uani d P 0.28 C
C7 0.4284(4) 0.750(2) 0.1223(4) 0.112(4) Uani d P 0.72 C
C7* 0.4350(10) 0.658(6) 0.1314(8) 0.0691 Uani d P 0.28 C
C8 0.4620(6) 0.801(2) 0.0896(4) 0.121(3) Uani d P 0.72 C
C8* 0.4470(10) 0.735(5) 0.0884(6) 0.0619 Uani d P 0.28 C
C9 0.5140(4) 0.642(2) 0.0783(2) 0.087(2) Uani d P 0.72 C
C9* 0.4882(6) 0.581(3) 0.0702(4) 0.0443 Uani d P 0.28 C
C10 0.5349(4) 0.442(2) 0.1043(3) 0.104(2) Uani d P 0.72 C
C10* 0.5133(7) 0.383(3) 0.0916(4) 0.0594 Uani d P 0.28 C
C11 0.5024(6) 0.385(2) 0.1398(3) 0.139(4) Uani d P 0.72 C
C11* 0.4980(10) 0.345(4) 0.1286(7) 0.0682 Uani d P 0.28 C
C12 0.5488(4) 0.7110(10) 0.0431(2) 0.093(2) Uani d P 0.72 C
C12* 0.5019(8) 0.631(2) 0.0258(4) 0.058(4) Uani d P 0.28 C
C13 0.5910(4) 0.5640(10) 0.0253(2) 0.087(2) Uani d P 0.72 C
C13* 0.5510(7) 0.460(2) 0.0055(4) 0.047(4) Uani d P 0.28 C
C14 0.6210(2) 0.6470(10) -0.00920(10) 0.1030(10) Uani d . 1.00 C
C15 0.6991(2) 0.5292(8) -0.05840(10) 0.1040(10) Uani d . 1.00 C
C16 0.7475(2) 0.3280(10) -0.06440(10) 0.133(2) Uani d . 1.00 C
C17 0.7821(2) 0.3570(10) -0.10280(10) 0.1030(10) Uani d . 1.00 C
C18 0.7665(2) 0.1945(8) -0.1351(2) 0.1010(10) Uani d . 1.00 C
C19 0.7962(2) 0.2135(9) -0.17110(10) 0.0930(10) Uani d . 1.00 C
C20 0.8447(2) 0.4040(10) -0.17420(10) 0.0990(10) Uani d . 1.00 C
C21 0.8604(2) 0.5702(9) -0.1430(2) 0.1100(10) Uani d . 1.00 C
C22 0.8284(2) 0.5440(10) -0.10740(10) 0.1120(10) Uani d . 1.00 C
C23 0.7292(2) -0.1020(10) -0.20230(10) 0.131(2) Uani d . 1.00 C
C24 0.9149(2) 0.6240(10) -0.21810(10) 0.142(2) Uani d . 1.00 C
H5 0.6557 0.2835 -0.0168 0.1091 Uiso calc . 1.00 H
H7 0.3922 0.8537 0.1282 0.1346 Uiso calc P 0.72 H
H8 0.4500 0.9500 0.0733 0.1453 Uiso calc P 0.72 H
H10 0.5715 0.3410 0.0983 0.1245 Uiso calc P 0.72 H
H11 0.5163 0.2484 0.1576 0.1668 Uiso calc P 0.72 H
H12 0.5401 0.8820 0.0317 0.1116 Uiso calc P 0.72 H
H13 0.6015 0.3934 0.0363 0.1042 Uiso calc P 0.72 H
H15A 0.7190 0.6959 -0.0526 0.1253 Uiso calc . 1.00 H
H15B 0.6746 0.5451 -0.0822 0.1253 Uiso calc . 1.00 H
H16A 0.7283 0.1565 -0.0640 0.1597 Uiso calc . 1.00 H
H16B 0.7775 0.3417 -0.0430 0.1597 Uiso calc . 1.00 H
H18 0.7340 0.0649 -0.1323 0.1206 Uiso calc . 1.00 H
H21 0.8926 0.7013 -0.1456 0.1324 Uiso calc . 1.00 H
H22 0.8391 0.6602 -0.0859 0.1350 Uiso calc . 1.00 H
H23A 0.6930 0.0065 -0.1987 0.1572 Uiso calc . 1.00 H
H23B 0.7333 -0.2259 -0.1809 0.1572 Uiso calc . 1.00 H
H23C 0.7249 -0.1982 -0.2266 0.1572 Uiso calc . 1.00 H
H24A 0.9310 0.6053 -0.2442 0.1708 Uiso calc . 1.00 H
H24B 0.9489 0.6204 -0.1992 0.1708 Uiso calc . 1.00 H
H24C 0.8932 0.7903 -0.2163 0.1708 Uiso calc . 1.00 H
H7* 0.4061 0.7631 0.1455 0.0830 Uiso calc P 0.28 H
H8* 0.4265 0.8809 0.0757 0.0743 Uiso calc P 0.28 H
H10* 0.5427 0.2652 0.0798 0.0713 Uiso calc P 0.28 H
H11* 0.5202 0.1993 0.1410 0.0818 Uiso calc P 0.28 H
H12* 0.5113 0.8154 0.0220 0.0695 Uiso calc P 0.28 H
H13* 0.5629 0.3133 0.0221 0.0558 Uiso calc P 0.28 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.148 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, 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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 O3 C23 . . 116.6(4) ?
C20 O4 C24 . . 118.0(4) ?
C14 N5 C15 . . 122.2(3) ?
C14 N5 H5 . . 118.9 no
C15 N5 H5 . . 118.9 no
Cl C6 C7 . . 123.7(9) ?
Cl C6 C11 . . 114.3(9) ?
C7 C6 C11 . . 121.0(10) ?
C6 C7 C8 . . 119.0(10) ?
C6 C7 H7 . . 120.3 no
C8 C7 H7 . . 120.7 no
C7 C8 C9 . . 122.0(10) ?
C7 C8 H8 . . 118.4 no
C9 C8 H8 . . 118.8 no
C8 C9 C10 . . 118.1(8) ?
C8 C9 C12 . . 119.9(8) ?
C10 C9 C12 . . 121.6(7) ?
C9 C10 C11 . . 121.2(8) ?
C9 C10 H10 . . 119.4 no
C11 C10 H10 . . 119.4 no
C6 C11 C10 . . 116.8(10) ?
C6 C11 H11 . . 121.7 no
C10 C11 H11 . . 121.5 no
C9 C12 C13 . . 127.2(6) yes
C9 C12 H12 . . 116.4 no
C13 C12 H12 . . 116.4 no
C12 C13 C14 . . 122.7(6) yes
C12 C13 H13 . . 118.6 no
C14 C13 H13 . . 118.7 no
O2 C14 N5 . . 123.5(4) ?
O2 C14 C13 . . 119.3(5) ?
N5 C14 C13 . . 115.4(5) ?
N5 C15 C16 . . 113.2(3) ?
N5 C15 H15A . . 108.6 no
N5 C15 H15B . . 108.5 no
C16 C15 H15A . . 108.6 no
C16 C15 H15B . . 108.4 no
H15A C15 H15B . . 109.5 no
C15 C16 C17 . . 114.5(4) ?
C15 C16 H16A . . 108.3 no
C15 C16 H16B . . 108.1 no
C17 C16 H16A . . 108.3 no
C17 C16 H16B . . 108.1 no
H16A C16 H16B . . 109.5 no
C16 C17 C18 . . 120.3(4) ?
C16 C17 C22 . . 121.7(4) ?
C18 C17 C22 . . 117.9(4) ?
C17 C18 C19 . . 122.8(4) ?
C17 C18 H18 . . 118.6 no
C19 C18 H18 . . 118.6 no
O3 C19 C18 . . 126.1(4) ?
O3 C19 C20 . . 116.5(4) ?
C18 C19 C20 . . 117.4(4) ?
O4 C20 C19 . . 114.7(4) ?
O4 C20 C21 . . 124.2(4) ?
C19 C20 C21 . . 121.1(4) ?
C20 C21 C22 . . 119.2(4) ?
C20 C21 H21 . . 120.4 no
C22 C21 H21 . . 120.4 no
C17 C22 C21 . . 121.6(4) ?
C17 C22 H22 . . 119.2 no
C21 C22 H22 . . 119.2 no
O3 C23 H23A . . 109.4 no
O3 C23 H23B . . 109.5 no
O3 C23 H23C . . 109.5 no
H23A C23 H23B . . 109.4 no
H23A C23 H23C . . 109.5 no
H23B C23 H23C . . 109.5 no
O4 C24 H24A . . 109.5 no
O4 C24 H24B . . 109.6 no
O4 C24 H24C . . 109.5 no
H24A C24 H24B . . 109.4 no
H24A C24 H24C . . 109.4 no
H24B C24 H24C . . 109.5 no
Cl* C6* C7* . . 109(2) ?
Cl* C6* C11* . . 140(2) ?
C7* C6* C11* . . 109(2) ?
C6* C7* C8* . . 125(2) ?
C6* C7* H7* . . 117.3 no
C8* C7* H7* . . 117.0 no
C7* C8* C9* . . 114.0(10) ?
C7* C8* H8* . . 122.9 no
C9* C8* H8* . . 122.6 no
C8* C9* C10* . . 116.0(10) ?
C8* C9* C12* . . 119.0(10) ?
C10* C9* C12* . . 124.0(10) ?
C9* C10* C11* . . 121.0(10) ?
C9* C10* H10* . . 119.2 no
C11* C10* H10* . . 119.2 no
C6* C11* C10* . . 132(2) ?
C6* C11* H11* . . 113.7 no
C10* C11* H11* . . 113.8 no
C9* C12* C13* . . 119.0(10) ?
C9* C12* C13* . 3_665 116.0(10) yes
C9* C12* H12* . . 109.4 no
C13* C12* C13* . 3_665 91.3(10) yes
C13* C12* H12* . . 109.4 no
C13* C12* H12* 3_665 . 109.4 no
C12* C13* C12* . 3_665 88.7(10) yes
C12* C13* H13* . . 110.1 no
C12* C13* H13* 3_665 . 110.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C6 . 1.690(10) yes
O2 C14 . 1.208(6) ?
O3 C19 . 1.336(6) ?
O3 C23 . 1.425(6) ?
O4 C20 . 1.372(5) ?
O4 C24 . 1.413(6) ?
N5 C14 . 1.329(6) ?
N5 C15 . 1.456(5) ?
N5 H5 . 0.950 no
C6 C7 . 1.38(2) ?
C6 C11 . 1.43(2) ?
C7 C8 . 1.35(2) ?
C7 H7 . 0.950 no
C8 C9 . 1.420(10) ?
C8 H8 . 0.953 no
C9 C10 . 1.390(10) ?
C9 C12 . 1.450(10) ?
C10 C11 . 1.420(10) ?
C10 H10 . 0.950 no
C11 H11 . 0.948 no
C12 C13 . 1.310(10) yes
C12 H12 . 0.951 no
C13 C14 . 1.399(8) ?
C13 H13 . 0.950 no
C15 C16 . 1.450(7) ?
C15 H15A . 0.949 no
C15 H15B . 0.950 no
C16 C17 . 1.508(7) ?
C16 H16A . 0.949 no
C16 H16B . 0.951 no
C17 C18 . 1.389(7) ?
C17 C22 . 1.366(7) ?
C18 C19 . 1.383(7) ?
C18 H18 . 0.950 no
C19 C20 . 1.403(7) ?
C20 C21 . 1.372(7) ?
C21 C22 . 1.396(7) ?
C21 H21 . 0.950 no
C22 H22 . 0.950 no
C23 H23A . 0.950 no
C23 H23B . 0.950 no
C23 H23C . 0.950 no
C24 H24A . 0.951 no
C24 H24B . 0.950 no
C24 H24C . 0.950 no
Cl* C6* . 1.76(3) yes
C6* C7* . 1.29(4) ?
C6* C11* . 1.22(3) ?
C7* C8* . 1.52(3) ?
C7* H7* . 0.949 no
C8* C9* . 1.32(3) ?
C8* H8* . 0.944 no
C9* C10* . 1.32(2) ?
C9* C12* . 1.55(2) ?
C10* C11* . 1.30(3) ?
C10* H10* . 0.949 no
C11* H11* . 0.952 no
C12* C13* . 1.52(2) ?
C12* C13* 3_665 1.59(2) yes
C12* H12* . 0.950 no
C13* H13* . 0.950 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N5 H5 O2 1_545 0.95 2.11 2.993(4) 155 yes
