#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103824.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_2103824
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                 91.313(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.210(4)
_cell_length_b                   4.9818(12)
_cell_length_c                   33.657(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      11.7
_cell_measurement_theta_min      10.0
_cell_volume                     3555.4(12)
_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  0.018
_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            5123
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.51
_diffrn_standards_decay_%        1.93
_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    1.292
_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         0.11
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4103
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.0020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0719P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1901
_reflns_number_gt                1093
_reflns_number_total             4103
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm0063.cif
_cod_data_source_block           Id
_cod_original_cell_volume        3554.7(12)
_cod_original_formula_sum        'C19 H20 Cl N O3 '
_cod_database_code               2103824
_cod_database_fobs_code          2103824
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 0.4106(4) 0.472(2) 0.1897(2) 0.179(2) Uani d P 0.74 Cl
Cl* 0.4296(9) 0.432(4) 0.1974(2) 0.129(5) Uani d P 0.26 Cl
O2 0.6246(2) 0.8848(6) -0.01723(8) 0.1260(10) Uani d . 1.00 O
O3 0.78410(10) 0.0592(6) -0.20338(9) 0.1141(9) Uani d . 1.00 O
O4 0.87330(10) 0.4031(6) -0.21090(8) 0.1191(9) Uani d . 1.00 O
N5 0.65770(10) 0.4625(6) -0.02631(8) 0.0896(9) Uani d . 1.00 N
C6 0.4501(7) 0.547(2) 0.1471(5) 0.111(5) Uani d P 0.74 C
C6* 0.4560(10) 0.468(6) 0.1499(8) 0.0607 Uani d P 0.26 C
C7 0.4297(4) 0.753(2) 0.1223(3) 0.108(3) Uani d P 0.74 C
C7* 0.4330(10) 0.650(7) 0.1313(8) 0.0691 Uani d P 0.26 C
C8 0.4628(5) 0.805(2) 0.0890(3) 0.115(3) Uani d P 0.74 C
C8* 0.4480(10) 0.726(4) 0.0884(6) 0.0619 Uani d P 0.26 C
C9 0.5148(4) 0.6420(10) 0.0781(2) 0.087(2) Uani d P 0.74 C
C9* 0.4877(7) 0.591(3) 0.0696(4) 0.0443 Uani d P 0.26 C
C10 0.5350(4) 0.4450(10) 0.1034(3) 0.104(2) Uani d P 0.74 C
C10* 0.5125(8) 0.383(4) 0.0918(5) 0.0594 Uani d P 0.26 C
C11 0.5054(6) 0.387(3) 0.1373(5) 0.132(3) Uani d P 0.74 C
C11* 0.4900(10) 0.350(6) 0.1338(8) 0.0682 Uani d P 0.26 C
C12 0.5497(4) 0.7120(10) 0.0425(2) 0.088(2) Uani d P 0.74 C
C12* 0.5021(8) 0.634(2) 0.0258(4) 0.057(5) Uani d P 0.26 C
C13 0.5914(3) 0.5600(10) 0.0247(2) 0.084(2) Uani d P 0.74 C
C13* 0.5490(7) 0.459(2) 0.0049(4) 0.054(4) Uani d P 0.26 C
C14 0.6224(2) 0.6479(9) -0.00940(10) 0.1000(10) Uani d . 1.00 C
C15 0.6989(2) 0.5286(7) -0.05890(10) 0.1020(10) Uani d . 1.00 C
C16 0.7477(2) 0.3275(10) -0.06450(10) 0.132(2) Uani d . 1.00 C
C17 0.7824(2) 0.3549(10) -0.10290(10) 0.1000(10) Uani d . 1.00 C
C18 0.7664(2) 0.1911(8) -0.1352(2) 0.1010(10) Uani d . 1.00 C
C19 0.7969(2) 0.2091(9) -0.17100(10) 0.0890(10) Uani d . 1.00 C
C20 0.8447(2) 0.4005(10) -0.17470(10) 0.0970(10) Uani d . 1.00 C
C21 0.8600(2) 0.5648(9) -0.1438(2) 0.1090(10) Uani d . 1.00 C
C22 0.8286(2) 0.5416(9) -0.10770(10) 0.1120(10) Uani d . 1.00 C
C23 0.7297(2) -0.1067(10) -0.20230(10) 0.127(2) Uani d . 1.00 C
C24 0.9150(2) 0.6170(10) -0.21840(10) 0.140(2) Uani d . 1.00 C
H5 0.6562 0.2828 -0.0169 0.1076 Uiso calc . 1.00 H
H7 0.3935 0.8553 0.1284 0.1294 Uiso calc P 0.74 H
H7* 0.4033 0.7587 0.1444 0.0829 Uiso calc P 0.26 H
H8 0.4507 0.9529 0.0727 0.1386 Uiso calc P 0.74 H
H8* 0.4270 0.8720 0.0759 0.0742 Uiso calc P 0.26 H
H10 0.5713 0.3438 0.0968 0.1250 Uiso calc P 0.74 H
H10* 0.5427 0.2651 0.0811 0.0713 Uiso calc P 0.26 H
H11 0.5199 0.2475 0.1543 0.1592 Uiso calc P 0.74 H
H11* 0.5089 0.2049 0.1483 0.0818 Uiso calc P 0.26 H
H12 0.5415 0.8833 0.0311 0.1053 Uiso calc P 0.74 H
H12* 0.5118 0.8175 0.0214 0.0688 Uiso calc P 0.26 H
H13 0.6008 0.3873 0.0351 0.1005 Uiso calc P 0.74 H
H13* 0.5605 0.3128 0.0216 0.0647 Uiso calc P 0.26 H
H15A 0.6741 0.5416 -0.0827 0.1227 Uiso calc . 1.00 H
H15B 0.7185 0.6966 -0.0535 0.1227 Uiso calc . 1.00 H
H16A 0.7776 0.3424 -0.0431 0.1581 Uiso calc . 1.00 H
H16B 0.7287 0.1552 -0.0640 0.1581 Uiso calc . 1.00 H
H18 0.7336 0.0630 -0.1325 0.1210 Uiso calc . 1.00 H
H21 0.8921 0.6960 -0.1466 0.1306 Uiso calc . 1.00 H
H22 0.8396 0.6579 -0.0863 0.1341 Uiso calc . 1.00 H
H23A 0.6934 0.0021 -0.1992 0.1529 Uiso calc . 1.00 H
H23B 0.7258 -0.2051 -0.2264 0.1529 Uiso calc . 1.00 H
H23C 0.7336 -0.2279 -0.1806 0.1529 Uiso calc . 1.00 H
H24A 0.9485 0.6149 -0.1992 0.1685 Uiso calc . 1.00 H
H24B 0.9317 0.5966 -0.2442 0.1685 Uiso calc . 1.00 H
H24C 0.8930 0.7822 -0.2169 0.1685 Uiso calc . 1.00 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 . . 116.8(3) ?
C20 O4 C24 . . 117.2(3) ?
C14 N5 C15 . . 121.4(3) ?
C14 N5 H5 . . 119.3 no
C15 N5 H5 . . 119.3 no
Cl C6 C7 . . 120.0(10) ?
Cl C6 C11 . . 118.0(10) ?
C7 C6 C11 . . 120.0(10) ?
C6 C7 C8 . . 118.6(10) ?
C6 C7 H7 . . 120.7 no
C8 C7 H7 . . 120.7 no
C7 C8 C9 . . 121.4(8) ?
C7 C8 H8 . . 119.1 no
C9 C8 H8 . . 119.5 no
C8 C9 C10 . . 119.0(7) ?
C8 C9 C12 . . 119.1(7) ?
C10 C9 C12 . . 121.5(7) ?
C9 C10 C11 . . 122.5(9) ?
C9 C10 H10 . . 118.8 no
C11 C10 H10 . . 118.7 no
C6 C11 C10 . . 117.0(10) ?
C6 C11 H11 . . 121.0 no
C10 C11 H11 . . 121.2 no
C9 C12 C13 . . 126.5(6) yes
C9 C12 H12 . . 116.7 no
C13 C12 H12 . . 116.8 no
C12 C13 C14 . . 121.7(5) yes
C12 C13 H13 . . 119.2 no
C14 C13 H13 . . 119.1 no
O2 C14 N5 . . 124.1(4) ?
O2 C14 C13 . . 120.1(4) ?
N5 C14 C13 . . 114.4(4) ?
N5 C15 C16 . . 112.5(3) ?
N5 C15 H15A . . 108.7 no
N5 C15 H15B . . 108.7 no
C16 C15 H15A . . 108.7 no
C16 C15 H15B . . 108.8 no
H15A C15 H15B . . 109.5 no
C15 C16 C17 . . 114.2(4) ?
C15 C16 H16A . . 108.2 no
C15 C16 H16B . . 108.4 no
C17 C16 H16A . . 108.2 no
C17 C16 H16B . . 108.3 no
H16A C16 H16B . . 109.5 no
C16 C17 C18 . . 120.1(4) ?
C16 C17 C22 . . 122.0(4) ?
C18 C17 C22 . . 117.9(4) ?
C17 C18 C19 . . 122.1(4) ?
C17 C18 H18 . . 118.9 no
C19 C18 H18 . . 118.9 no
O3 C19 C18 . . 125.5(4) ?
O3 C19 C20 . . 116.1(4) ?
C18 C19 C20 . . 118.3(4) ?
O4 C20 C19 . . 114.8(4) ?
O4 C20 C21 . . 124.9(4) ?
C19 C20 C21 . . 120.3(4) ?
C20 C21 C22 . . 120.2(4) ?
C20 C21 H21 . . 119.9 no
C22 C21 H21 . . 119.9 no
C17 C22 C21 . . 121.1(4) ?
C17 C22 H22 . . 119.4 no
C21 C22 H22 . . 119.5 no
O3 C23 H23A . . 109.5 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 . . 109.4 no
O4 C24 H24B . . 109.4 no
O4 C24 H24C . . 109.4 no
H24A C24 H24B . . 109.5 no
H24A C24 H24C . . 109.5 no
H24B C24 H24C . . 109.5 no
Cl* C6* C7* . . 115(2) ?
Cl* C6* C11* . . 130(2) ?
C7* C6* C11* . . 114(3) ?
C6* C7* C8* . . 126(2) ?
C6* C7* H7* . . 116.9 no
C8* C7* H7* . . 116.5 no
C7* C8* C9* . . 119.0(10) ?
C7* C8* H8* . . 120.4 no
C9* C8* H8* . . 120.1 no
C8* C9* C10* . . 112.0(10) ?
C8* C9* C12* . . 124.0(10) ?
C10* C9* C12* . . 123.0(10) ?
C9* C10* C11* . . 117.0(10) ?
C9* C10* H10* . . 120.9 no
C11* C10* H10* . . 121.2 no
C6* C11* C10* . . 129(2) ?
C6* C11* H11* . . 115.5 no
C10* C11* H11* . . 115.1 no
C9* C12* C13* . . 121.0(10) ?
C9* C12* C13* . 3_665 116.0(10) yes
C9* C12* H12* . . 109.5 no
C13* C12* C13* . 3_665 88.0(10) yes
C13* C12* H12* . . 109.6 no
C13* C12* H12* 3_665 . 109.6 no
C12* C13* C12* . 3_665 91.0(10) yes
C12* C13* H13* . . 109.3 no
C12* C13* H13* 3_665 . 109.4 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 . 1.72(2) yes
O2 C14 . 1.210(5) ?
O3 C19 . 1.343(5) ?
O3 C23 . 1.421(6) ?
O4 C20 . 1.374(5) ?
O4 C24 . 1.412(6) ?
N5 C14 . 1.325(5) ?
N5 C15 . 1.457(5) ?
N5 H5 . 0.950 no
C6 C7 . 1.38(2) ?
C6 C11 . 1.46(2) ?
C7 C8 . 1.360(10) ?
C7 H7 . 0.950 no
C8 C9 . 1.420(10) ?
C8 H8 . 0.951 no
C9 C10 . 1.360(10) ?
C9 C12 . 1.464(9) ?
C10 C11 . 1.35(2) ?
C10 H10 . 0.951 no
C11 H11 . 0.948 no
C12 C13 . 1.319(9) yes
C12 H12 . 0.950 no
C13 C14 . 1.404(7) ?
C13 H13 . 0.950 no
C15 C16 . 1.456(6) ?
C15 H15A . 0.950 no
C15 H15B . 0.950 no
C16 C17 . 1.506(6) ?
C16 H16A . 0.951 no
C16 H16B . 0.949 no
C17 C18 . 1.394(7) ?
C17 C22 . 1.364(7) ?
C18 C19 . 1.385(7) ?
C18 H18 . 0.950 no
C19 C20 . 1.400(6) ?
C20 C21 . 1.356(7) ?
C21 C22 . 1.403(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 . 0.950 no
C24 H24B . 0.950 no
C24 H24C . 0.950 no
Cl* C6* . 1.71(3) yes
C6* C7* . 1.20(4) ?
C6* C11* . 1.09(4) ?
C7* C8* . 1.53(4) ?
C7* H7* . 0.953 no
C8* C9* . 1.26(3) ?
C8* H8* . 0.945 no
C9* C10* . 1.37(2) ?
C9* C12* . 1.53(2) ?
C10* C11* . 1.51(3) ?
C10* H10* . 0.948 no
C11* H11* . 0.954 no
C12* C13* . 1.51(2) yes
C12* C13* 3_665 1.55(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 2.09 2.979(4) 155 yes
