#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103822.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_2103822
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         'C38 H40 Cl2 N2 O6 '
_chemical_formula_sum            'C38 H40 Cl2 N2 O6'
_chemical_formula_weight         691.62
_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                 92.166(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.835(3)
_cell_length_b                   4.9657(10)
_cell_length_c                   33.352(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      13.9
_cell_measurement_theta_min      10.1
_cell_volume                     3448.1(9)
_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  0.017
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            5877
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        0.78
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456.0
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.23
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3951
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0441P)²+1.8600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1252
_reflns_number_gt                1805
_reflns_number_total             3951
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm0063.cif
_cod_data_source_block           II
_cod_original_formula_sum        'C38 H40 Cl2 N2 O6 '
_cod_database_code               2103822
_cod_database_fobs_code          2103822
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_occupancy
_atom_site_type_symbol
Cl 0.43417(4) 0.3456(2) 0.19711(2) 0.0970(3) Uani d 1.00 Cl
O2 0.60664(8) 0.8679(3) -0.01459(5) 0.0562(4) Uani d 1.00 O
O3 0.78102(9) 0.1693(4) -0.20197(6) 0.0816(6) Uani d 1.00 O
O4 0.87070(9) 0.5192(4) -0.20785(5) 0.0805(6) Uani d 1.00 O
N5 0.65527(9) 0.4692(4) -0.02370(5) 0.0510(5) Uani d 1.00 N
C6 0.45660(10) 0.4331(6) 0.14907(7) 0.0606(7) Uani d 1.00 C
C7 0.42830(10) 0.6467(6) 0.12983(8) 0.0690(8) Uani d 1.00 C
C8 0.44510(10) 0.7104(5) 0.09113(7) 0.0618(7) Uani d 1.00 C
C9 0.48930(10) 0.5556(5) 0.07105(6) 0.0443(5) Uani d 1.00 C
C10 0.51800(10) 0.3474(5) 0.09164(7) 0.0593(7) Uani d 1.00 C
C11 0.50230(10) 0.2860(6) 0.13066(7) 0.0682(8) Uani d 1.00 C
C12 0.50140(10) 0.6219(4) 0.02773(6) 0.0433(5) Uani d 1.00 C
C13 0.55200(10) 0.4626(4) 0.00509(6) 0.0425(5) Uani d 1.00 C
C14 0.60710(10) 0.6217(5) -0.01099(6) 0.0424(5) Uani d 1.00 C
C15 0.70190(10) 0.5710(5) -0.05156(8) 0.0624(7) Uani d 1.00 C
C16 0.75370(10) 0.3745(6) -0.05876(8) 0.0767(9) Uani d 1.00 C
C17 0.78680(10) 0.4223(6) -0.09782(7) 0.0596(7) Uani d 1.00 C
C18 0.76790(10) 0.2718(5) -0.13140(8) 0.0600(7) Uani d 1.00 C
C19 0.79630(10) 0.3088(5) -0.16789(8) 0.0580(7) Uani d 1.00 C
C20 0.84470(10) 0.5024(6) -0.17076(7) 0.0587(7) Uani d 1.00 C
C21 0.86270(10) 0.6534(6) -0.13791(8) 0.0649(7) Uani d 1.00 C
C22 0.83380(10) 0.6123(6) -0.10165(7) 0.0649(7) Uani d 1.00 C
C23 0.7259(2) -0.0005(7) -0.20220(10) 0.0940(10) Uani d 1.00 C
C24 0.9149(2) 0.7289(7) -0.21436(9) 0.0910(10) Uani d 1.00 C
H5 0.6593 0.2891 -0.0143 0.0615 Uiso calc 1.00 H
H7 0.3971 0.7513 0.1429 0.0828 Uiso calc 1.00 H
H8 0.4261 0.8627 0.0781 0.0745 Uiso calc 1.00 H
H10 0.5493 0.2413 0.0789 0.0712 Uiso calc 1.00 H
H11 0.5234 0.1422 0.1446 0.0818 Uiso calc 1.00 H
H12 0.5099 0.8091 0.0254 0.0519 Uiso calc 1.00 H
H13 0.5668 0.3115 0.0202 0.0510 Uiso calc 1.00 H
H15A 0.7206 0.7310 -0.0407 0.0751 Uiso calc 1.00 H
H15B 0.6801 0.6110 -0.0764 0.0751 Uiso calc 1.00 H
H16A 0.7357 0.1990 -0.0594 0.0922 Uiso calc 1.00 H
H16B 0.7849 0.3868 -0.0373 0.0922 Uiso calc 1.00 H
H18 0.7348 0.1410 -0.1293 0.0719 Uiso calc 1.00 H
H21 0.8951 0.7873 -0.1400 0.0778 Uiso calc 1.00 H
H22 0.8470 0.7172 -0.0790 0.0783 Uiso calc 1.00 H
H23A 0.6890 0.1041 -0.1972 0.1128 Uiso calc 1.00 H
H23B 0.7315 -0.1336 -0.1819 0.1128 Uiso calc 1.00 H
H23C 0.7208 -0.0860 -0.2276 0.1128 Uiso calc 1.00 H
H24A 0.9294 0.7177 -0.2410 0.1090 Uiso calc 1.00 H
H24B 0.9506 0.7119 -0.1959 0.1090 Uiso calc 1.00 H
H24C 0.8946 0.8976 -0.2106 0.1090 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 . . 118.0(2) ?
C20 O4 C24 . . 117.8(2) ?
C14 N5 C15 . . 122.0(2) ?
C14 N5 H5 . . 119.0 no
C15 N5 H5 . . 119.0 no
Cl C6 C7 . . 120.1(2) ?
Cl C6 C11 . . 119.8(2) ?
C7 C6 C11 . . 120.1(2) ?
C6 C7 C8 . . 119.8(3) ?
C6 C7 H7 . . 120.1 no
C8 C7 H7 . . 120.2 no
C7 C8 C9 . . 121.1(2) ?
C7 C8 H8 . . 119.4 no
C9 C8 H8 . . 119.5 no
C8 C9 C10 . . 117.5(2) ?
C8 C9 C12 . . 118.5(2) ?
C10 C9 C12 . . 124.0(2) ?
C9 C10 C11 . . 121.6(2) ?
C9 C10 H10 . . 119.3 no
C11 C10 H10 . . 119.2 no
C6 C11 C10 . . 119.9(2) ?
C6 C11 H11 . . 120.1 no
C10 C11 H11 . . 120.1 no
C9 C12 C13 . . 119.9(2) yes
C9 C12 C13 . 3_665 117.6(2) yes
C9 C12 H12 . . 109.3 no
C13 C12 C13 . 3_665 90.0(2) yes
C13 C12 H12 . . 109.2 no
C13 C12 H12 3_665 . 109.2 no
C12 C13 C12 . 3_665 90.0(2) yes
C12 C13 C14 . . 116.7(2) yes
C12 C13 H13 . . 111.2 no
C12 C13 C14 3_665 . 114.6(2) yes
C12 C13 H13 3_665 . 111.3 no
C14 C13 H13 . . 111.4 no
O2 C14 N5 . . 122.3(2) ?
O2 C14 C13 . . 123.6(2) ?
N5 C14 C13 . . 113.9(2) ?
N5 C15 C16 . . 112.4(2) ?
N5 C15 H15A . . 108.6 no
N5 C15 H15B . . 108.7 no
C16 C15 H15A . . 108.8 no
C16 C15 H15B . . 108.8 no
H15A C15 H15B . . 109.5 no
C15 C16 C17 . . 113.2(2) ?
C15 C16 H16A . . 108.5 no
C15 C16 H16B . . 108.5 no
C17 C16 H16A . . 108.6 no
C17 C16 H16B . . 108.5 no
H16A C16 H16B . . 109.5 no
C16 C17 C18 . . 119.0(2) ?
C16 C17 C22 . . 122.6(2) ?
C18 C17 C22 . . 118.4(2) ?
C17 C18 C19 . . 121.3(2) ?
C17 C18 H18 . . 119.4 no
C19 C18 H18 . . 119.4 no
O3 C19 C18 . . 124.9(2) ?
O3 C19 C20 . . 116.1(2) ?
C18 C19 C20 . . 119.0(2) ?
O4 C20 C19 . . 114.5(2) ?
O4 C20 C21 . . 125.7(2) ?
C19 C20 C21 . . 119.9(2) ?
C20 C21 C22 . . 120.2(2) ?
C20 C21 H21 . . 119.9 no
C22 C21 H21 . . 119.9 no
C17 C22 C21 . . 121.2(2) ?
C17 C22 H22 . . 119.3 no
C21 C22 H22 . . 119.5 no
O3 C23 H23A . . 109.5 no
O3 C23 H23B . . 109.3 no
O3 C23 H23C . . 109.4 no
H23A C23 H23B . . 109.6 no
H23A C23 H23C . . 109.7 no
H23B C23 H23C . . 109.4 no
O4 C24 H24A . . 109.5 no
O4 C24 H24B . . 109.4 no
O4 C24 H24C . . 109.5 no
H24A C24 H24B . . 109.4 no
H24A C24 H24C . . 109.6 no
H24B C24 H24C . . 109.5 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 . 1.741(3) yes
O2 C14 . 1.228(3) ?
O3 C19 . 1.359(3) ?
O3 C23 . 1.425(4) ?
O4 C20 . 1.372(3) ?
O4 C24 . 1.413(4) ?
N5 C14 . 1.340(3) ?
N5 C15 . 1.459(3) ?
N5 H5 . 0.950 no
C6 C7 . 1.362(4) ?
C6 C11 . 1.365(4) ?
C7 C8 . 1.386(4) ?
C7 H7 . 0.950 no
C8 C9 . 1.392(3) ?
C8 H8 . 0.951 no
C9 C10 . 1.366(3) ?
C9 C12 . 1.512(3) ?
C10 C11 . 1.388(3) ?
C10 H10 . 0.951 no
C11 H11 . 0.951 no
C12 C13 . 1.538(3) yes
C12 C13 3_665 1.587(3) yes
C12 H12 . 0.951 no
C13 C14 . 1.509(3) ?
C13 H13 . 0.949 no
C15 C16 . 1.482(4) ?
C15 H15A . 0.951 no
C15 H15B . 0.949 no
C16 C17 . 1.515(4) ?
C16 H16A . 0.949 no
C16 H16B . 0.950 no
C17 C18 . 1.390(4) ?
C17 C22 . 1.370(4) ?
C18 C19 . 1.386(4) ?
C18 H18 . 0.951 no
C19 C20 . 1.398(4) ?
C20 C21 . 1.368(4) ?
C21 C22 . 1.386(4) ?
C21 H21 . 0.952 no
C22 H22 . 0.951 no
C23 H23A . 0.948 no
C23 H23B . 0.951 no
C23 H23C . 0.950 no
C24 H24A . 0.950 no
C24 H24B . 0.951 no
C24 H24C . 0.949 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 2.36 3.171(2) 143 yes
