#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103823.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_2103823
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(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.233(5)
_cell_length_b                   4.9827(14)
_cell_length_c                   33.664(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      13.6
_cell_measurement_theta_min      10.2
_cell_volume                     3560.6(14)
_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  0.014
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            5130
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        1.84
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.230
_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    1.290
_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         0.13
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4109
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                1133
_reflns_number_total             4109
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm0063.cif
_cod_data_source_block           Ic
_cod_original_formula_sum        'C19 H20 Cl N O3 '
_cod_database_code               2103823
_cod_database_fobs_code          2103823
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 0.4105(3) 0.478(2) 0.1897(2) 0.167(2) Uani d P 0.78 Cl
Cl* 0.4330(10) 0.427(5) 0.1977(4) 0.139(6) Uani d P 0.22 Cl
O2 0.62570(10) 0.8849(5) -0.01773(7) 0.1250(10) Uani d . 1.00 O
O3 0.78410(10) 0.0534(5) -0.20353(7) 0.1115(8) Uani d . 1.00 O
O4 0.87370(10) 0.3992(5) -0.21116(7) 0.1179(8) Uani d . 1.00 O
N5 0.65810(10) 0.4627(5) -0.02679(7) 0.0903(8) Uani d . 1.00 N
C6 0.4483(3) 0.549(2) 0.1466(3) 0.098(3) Uani d P 0.78 C
C6* 0.4650(10) 0.459(5) 0.1504(7) 0.0607 Uani d P 0.22 C
C7 0.4298(4) 0.755(2) 0.1215(3) 0.118(4) Uani d P 0.78 C
C7* 0.435(2) 0.676(7) 0.1310(10) 0.0691 Uani d P 0.22 C
C8 0.4641(4) 0.798(2) 0.0878(3) 0.121(3) Uani d P 0.78 C
C8* 0.4460(10) 0.748(6) 0.0890(9) 0.0619 Uani d P 0.22 C
C9 0.5155(3) 0.6450(10) 0.0777(2) 0.088(2) Uani d P 0.78 C
C9* 0.4876(8) 0.589(3) 0.0696(4) 0.0443 Uani d P 0.22 C
C10 0.5347(3) 0.4480(10) 0.1032(2) 0.102(2) Uani d P 0.78 C
C10* 0.5128(8) 0.383(4) 0.0919(5) 0.0594 Uani d P 0.22 C
C11 0.5018(4) 0.392(2) 0.1389(2) 0.122(3) Uani d P 0.78 C
C11* 0.5000(10) 0.351(5) 0.1256(7) 0.0682 Uani d P 0.22 C
C12 0.5505(3) 0.7111(9) 0.04180(10) 0.085(2) Uani d P 0.78 C
C12* 0.5021(8) 0.632(2) 0.0257(5) 0.052(5) Uani d P 0.22 C
C13 0.5917(3) 0.5621(9) 0.0246(2) 0.082(2) Uani d P 0.78 C
C13* 0.5491(8) 0.460(2) 0.0045(4) 0.052(4) Uani d P 0.22 C
C14 0.6235(2) 0.6498(8) -0.00950(10) 0.0940(10) Uani d . 1.00 C
C15 0.6990(2) 0.5256(6) -0.05970(10) 0.1030(10) Uani d . 1.00 C
C16 0.7484(2) 0.3246(8) -0.06490(10) 0.1290(10) Uani d . 1.00 C
C17 0.7828(2) 0.3518(9) -0.10380(10) 0.0960(10) Uani d . 1.00 C
C18 0.7667(2) 0.1875(7) -0.13540(10) 0.0960(10) Uani d . 1.00 C
C19 0.7966(2) 0.2048(8) -0.17110(10) 0.0880(10) Uani d . 1.00 C
C20 0.8450(2) 0.3942(8) -0.17510(10) 0.0950(10) Uani d . 1.00 C
C21 0.8604(2) 0.5613(7) -0.14410(10) 0.1050(10) Uani d . 1.00 C
C22 0.8294(2) 0.5421(8) -0.10800(10) 0.1110(10) Uani d . 1.00 C
C23 0.7300(2) -0.1122(8) -0.20260(10) 0.1260(10) Uani d . 1.00 C
C24 0.9158(2) 0.6135(9) -0.21910(10) 0.143(2) Uani d . 1.00 C
H5 0.6562 0.2831 -0.0174 0.1083 Uiso calc . 1.00 H
H7 0.3943 0.8633 0.1273 0.1419 Uiso calc P 0.78 H
H8 0.4516 0.9410 0.0706 0.1447 Uiso calc P 0.78 H
H10 0.5707 0.3441 0.0971 0.1226 Uiso calc P 0.78 H
H11 0.5153 0.2552 0.1566 0.1468 Uiso calc P 0.78 H
H12 0.5419 0.8809 0.0300 0.1021 Uiso calc P 0.78 H
H13 0.6008 0.3892 0.0351 0.0991 Uiso calc P 0.78 H
H15A 0.7183 0.6947 -0.0548 0.1241 Uiso calc . 1.00 H
H15B 0.6741 0.5350 -0.0834 0.1241 Uiso calc . 1.00 H
H16A 0.7296 0.1517 -0.0641 0.1549 Uiso calc . 1.00 H
H16B 0.7782 0.3419 -0.0436 0.1549 Uiso calc . 1.00 H
H18 0.7341 0.0587 -0.1324 0.1150 Uiso calc . 1.00 H
H21 0.8926 0.6920 -0.1472 0.1263 Uiso calc . 1.00 H
H22 0.8403 0.6587 -0.0865 0.1334 Uiso calc . 1.00 H
H23A 0.7338 -0.2336 -0.1809 0.1515 Uiso calc . 1.00 H
H23B 0.7262 -0.2102 -0.2267 0.1515 Uiso calc . 1.00 H
H23C 0.6936 -0.0037 -0.1995 0.1515 Uiso calc . 1.00 H
H24A 0.8936 0.7790 -0.2182 0.1713 Uiso calc . 1.00 H
H24B 0.9327 0.5903 -0.2448 0.1713 Uiso calc . 1.00 H
H24C 0.9490 0.6143 -0.1998 0.1713 Uiso calc . 1.00 H
H7* 0.4059 0.7817 0.1457 0.0829 Uiso calc P 0.22 H
H8* 0.4250 0.8945 0.0764 0.0742 Uiso calc P 0.22 H
H10* 0.5415 0.2637 0.0798 0.0713 Uiso calc P 0.22 H
H11* 0.5228 0.2016 0.1369 0.0818 Uiso calc P 0.22 H
H12* 0.5113 0.8160 0.0213 0.0627 Uiso calc P 0.22 H
H13* 0.5606 0.3130 0.0211 0.0618 Uiso calc P 0.22 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 . . 117.0(3) ?
C20 O4 C24 . . 118.3(3) ?
C14 N5 C15 . . 121.8(3) ?
C14 N5 H5 . . 119.1 no
C15 N5 H5 . . 119.1 no
Cl C6 C7 . . 122.6(7) ?
Cl C6 C11 . . 116.0(7) ?
C7 C6 C11 . . 121.3(8) ?
C6 C7 C8 . . 118.1(8) ?
C6 C7 H7 . . 120.9 no
C8 C7 H7 . . 121.0 no
C7 C8 C9 . . 123.5(9) ?
C7 C8 H8 . . 118.2 no
C9 C8 H8 . . 118.3 no
C8 C9 C10 . . 118.1(7) ?
C8 C9 C12 . . 119.8(7) ?
C10 C9 C12 . . 121.9(6) ?
C9 C10 C11 . . 121.6(6) ?
C9 C10 H10 . . 119.3 no
C11 C10 H10 . . 119.2 no
C6 C11 C10 . . 117.3(7) ?
C6 C11 H11 . . 121.3 no
C10 C11 H11 . . 121.4 no
C9 C12 C13 . . 126.9(5) yes
C9 C12 H12 . . 116.6 no
C13 C12 H12 . . 116.6 no
C12 C13 C14 . . 121.8(4) yes
C12 C13 H13 . . 119.1 no
C14 C13 H13 . . 119.1 no
O2 C14 N5 . . 123.8(3) ?
O2 C14 C13 . . 120.6(4) ?
N5 C14 C13 . . 114.7(4) ?
N5 C15 C16 . . 112.6(3) ?
N5 C15 H15A . . 108.7 no
N5 C15 H15B . . 108.7 no
C16 C15 H15A . . 108.7 no
C16 C15 H15B . . 108.7 no
H15A C15 H15B . . 109.5 no
C15 C16 C17 . . 113.7(3) ?
C15 C16 H16A . . 108.4 no
C15 C16 H16B . . 108.4 no
C17 C16 H16A . . 108.4 no
C17 C16 H16B . . 108.4 no
H16A C16 H16B . . 109.5 no
C16 C17 C18 . . 119.7(4) ?
C16 C17 C22 . . 120.6(3) ?
C18 C17 C22 . . 119.7(4) ?
C17 C18 C19 . . 121.7(3) ?
C17 C18 H18 . . 119.1 no
C19 C18 H18 . . 119.1 no
O3 C19 C18 . . 125.8(3) ?
O3 C19 C20 . . 115.6(3) ?
C18 C19 C20 . . 118.6(3) ?
O4 C20 C19 . . 115.9(3) ?
O4 C20 C21 . . 124.1(4) ?
C19 C20 C21 . . 120.0(4) ?
C20 C21 C22 . . 120.8(4) ?
C20 C21 H21 . . 119.6 no
C22 C21 H21 . . 119.6 no
C17 C22 C21 . . 119.2(3) ?
C17 C22 H22 . . 120.4 no
C21 C22 H22 . . 120.4 no
O3 C23 H23A . . 109.5 no
O3 C23 H23B . . 109.5 no
O3 C23 H23C . . 109.4 no
H23A C23 H23B . . 109.5 no
H23A C23 H23C . . 109.5 no
H23B C23 H23C . . 109.5 no
O4 C24 H24A . . 109.5 no
O4 C24 H24B . . 109.4 no
O4 C24 H24C . . 109.5 no
H24A C24 H24B . . 109.5 no
H24A C24 H24C . . 109.5 no
H24B C24 H24C . . 109.5 no
Cl* C6* C7* . . 108(2) ?
Cl* C6* C11* . . 144(2) ?
C7* C6* C11* . . 107(2) ?
C6* C7* C8* . . 122(2) ?
C6* C7* H7* . . 118.6 no
C8* C7* H7* . . 118.5 no
C7* C8* C9* . . 115(2) ?
C7* C8* H8* . . 122.0 no
C9* C8* H8* . . 122.3 no
C8* C9* C10* . . 115.0(10) ?
C8* C9* C12* . . 121.0(10) ?
C10* C9* C12* . . 123.0(10) ?
C9* C10* C11* . . 121.0(10) ?
C9* C10* H10* . . 118.8 no
C11* C10* H10* . . 119.4 no
C6* C11* C10* . . 137(2) ?
C6* C11* H11* . . 111.9 no
C10* C11* H11* . . 110.8 no
C9* C12* C13* . . 121.0(10) ?
C9* C12* C13* . 3_665 116.0(10) yes
C9* C12* H12* . . 109.4 no
C13* C12* C13* . 3_665 89.0(10) yes
C13* C12* H12* . . 109.4 no
C13* C12* H12* 3_665 . 109.3 no
C12* C13* C12* . 3_665 90.0(10) yes
C12* C13* H13* . . 108.9 no
C12* C13* H13* 3_665 . 109.0 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 . 1.710(10) yes
O2 C14 . 1.205(5) ?
O3 C19 . 1.347(5) ?
O3 C23 . 1.415(5) ?
O4 C20 . 1.371(4) ?
O4 C24 . 1.421(5) ?
N5 C14 . 1.329(5) ?
N5 C15 . 1.457(4) ?
N5 H5 . 0.950 no
C6 C7 . 1.380(10) ?
C6 C11 . 1.410(10) ?
C7 C8 . 1.380(10) ?
C7 H7 . 0.951 no
C8 C9 . 1.380(10) ?
C8 H8 . 0.952 no
C9 C10 . 1.361(9) ?
C9 C12 . 1.470(8) ?
C10 C11 . 1.430(10) ?
C10 H10 . 0.950 no
C11 H11 . 0.945 no
C12 C13 . 1.295(8) yes
C12 H12 . 0.950 no
C13 C14 . 1.415(6) ?
C13 H13 . 0.950 no
C15 C16 . 1.462(5) ?
C15 H15A . 0.950 no
C15 H15B . 0.950 no
C16 C17 . 1.520(5) ?
C16 H16A . 0.950 no
C16 H16B . 0.950 no
C17 C18 . 1.379(6) ?
C17 C22 . 1.380(6) ?
C18 C19 . 1.378(6) ?
C18 H18 . 0.950 no
C19 C20 . 1.404(6) ?
C20 C21 . 1.369(6) ?
C21 C22 . 1.401(6) ?
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* . 1.75(3) yes
C6* C7* . 1.41(4) ?
C6* C11* . 1.25(4) ?
C7* C8* . 1.49(5) ?
C7* H7* . 0.947 no
C8* C9* . 1.37(3) ?
C8* H8* . 0.946 no
C9* C10* . 1.37(2) ?
C9* C12* . 1.53(2) ?
C10* C11* . 1.19(3) ?
C10* H10* . 0.950 no
C11* H11* . 0.964 no
C12* C13* . 1.51(2) yes
C12* C13* 3_665 1.54(2) ?
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 2.977(3) 155 yes
