#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103821.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_2103821
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         345.81
_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                 91.298(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.150(4)
_cell_length_b                   4.9724(10)
_cell_length_c                   33.620(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      11.8
_cell_measurement_theta_min      10.1
_cell_volume                     3534.8(11)
_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  0.021
_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            6042
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        2.58
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_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         0.12
_refine_diff_density_min         -0.12
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4079
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.0000
_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         0.1578
_reflns_number_gt                1136
_reflns_number_total             4079
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm0063.cif
_cod_data_source_block           Ib
_cod_original_formula_sum        'C19 H20 Cl N O3 '
_cod_database_code               2103821
_cod_database_fobs_code          2103821
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 0.4125(4) 0.455(2) 0.1915(2) 0.183(3) Uani d P 0.66 Cl
O2 0.61960(10) 0.8808(5) -0.01651(7) 0.1227(9) Uani d . 1.00 O
O3 0.78370(10) 0.0816(6) -0.20296(8) 0.1183(8) Uani d . 1.00 O
O4 0.87260(10) 0.4270(5) -0.20950(7) 0.1205(8) Uani d . 1.00 O
N5 0.65600(10) 0.4633(5) -0.02516(7) 0.0865(8) Uani d . 1.00 N
C6 0.4475(7) 0.539(3) 0.1476(5) 0.118(7) Uani d P 0.66 C
C7 0.4287(6) 0.747(2) 0.1227(4) 0.119(5) Uani d P 0.66 C
C8 0.4612(5) 0.796(2) 0.0904(4) 0.115(3) Uani d P 0.66 C
C9 0.5129(4) 0.634(2) 0.0791(2) 0.088(2) Uani d P 0.66 C
C10 0.5344(4) 0.434(2) 0.1044(3) 0.109(2) Uani d P 0.66 C
C11 0.5010(7) 0.374(2) 0.1408(3) 0.140(4) Uani d P 0.66 C
C12 0.5467(4) 0.7050(10) 0.0436(2) 0.094(2) Uani d P 0.66 C
C13 0.5896(4) 0.5570(10) 0.0258(2) 0.090(2) Uani d P 0.66 C
C14 0.6180(2) 0.6436(9) -0.00920(10) 0.1010(10) Uani d . 1.00 C
C15 0.6986(2) 0.5343(6) -0.05660(10) 0.1030(10) Uani d . 1.00 C
C16 0.7475(2) 0.3346(9) -0.06320(10) 0.1350(10) Uani d . 1.00 C
C17 0.7822(2) 0.3648(9) -0.10170(10) 0.1040(10) Uani d . 1.00 C
C18 0.7660(2) 0.2052(7) -0.13440(10) 0.1000(10) Uani d . 1.00 C
C19 0.7964(2) 0.2308(9) -0.17010(10) 0.0930(10) Uani d . 1.00 C
C20 0.8443(2) 0.4198(9) -0.17340(10) 0.0970(10) Uani d . 1.00 C
C21 0.8598(2) 0.5819(7) -0.14200(10) 0.1090(10) Uani d . 1.00 C
C22 0.8285(2) 0.5529(8) -0.10610(10) 0.1140(10) Uani d . 1.00 C
C23 0.7288(2) -0.0843(9) -0.20260(10) 0.1390(10) Uani d . 1.00 C
C24 0.9145(2) 0.6393(9) -0.21730(10) 0.1380(10) Uani d . 1.00 C
Cl* 0.4294(7) 0.409(3) 0.1977(2) 0.129(3) Uani d P 0.34 Cl
C6* 0.4570(10) 0.469(6) 0.1496(7) 0.0607 Uani d P 0.34 C
C7* 0.4300(10) 0.661(5) 0.1304(7) 0.0691 Uani d P 0.34 C
C8* 0.4466(8) 0.718(3) 0.0887(5) 0.0619 Uani d P 0.34 C
C9* 0.4872(5) 0.579(2) 0.0699(3) 0.0443 Uani d P 0.34 C
C10* 0.5123(5) 0.384(3) 0.0915(3) 0.0594 Uani d P 0.34 C
C11* 0.4983(9) 0.336(3) 0.1290(5) 0.0682 Uani d P 0.34 C
C12* 0.4994(5) 0.628(2) 0.0258(3) 0.050(3) Uani d P 0.34 C
C13* 0.5504(5) 0.463(2) 0.0052(3) 0.045(3) Uani d P 0.34 C
H5 0.6553 0.2832 -0.0158 0.1040 Uiso calc . 1.00 H
H7 0.3930 0.8544 0.1289 0.1434 Uiso calc P 0.66 H
H8 0.4498 0.9442 0.0741 0.1381 Uiso calc P 0.66 H
H10 0.5707 0.3305 0.0979 0.1301 Uiso calc P 0.66 H
H11 0.5151 0.2405 0.1588 0.1734 Uiso calc P 0.66 H
H12 0.5369 0.8747 0.0320 0.1132 Uiso calc P 0.66 H
H13 0.6014 0.3878 0.0369 0.1079 Uiso calc P 0.66 H
H15A 0.6745 0.5552 -0.0806 0.1233 Uiso calc . 1.00 H
H15B 0.7185 0.7002 -0.0499 0.1233 Uiso calc . 1.00 H
H16A 0.7777 0.3470 -0.0418 0.1624 Uiso calc . 1.00 H
H16B 0.7284 0.1620 -0.0630 0.1624 Uiso calc . 1.00 H
H18 0.7333 0.0754 -0.1321 0.1206 Uiso calc . 1.00 H
H21 0.8917 0.7146 -0.1445 0.1306 Uiso calc . 1.00 H
H22 0.8397 0.6660 -0.0844 0.1368 Uiso calc . 1.00 H
H23A 0.6924 0.0244 -0.1992 0.1667 Uiso calc . 1.00 H
H23B 0.7250 -0.1789 -0.2271 0.1667 Uiso calc . 1.00 H
H23C 0.7325 -0.2095 -0.1813 0.1667 Uiso calc . 1.00 H
H24A 0.9486 0.6358 -0.1985 0.1654 Uiso calc . 1.00 H
H24B 0.9305 0.6198 -0.2434 0.1654 Uiso calc . 1.00 H
H24C 0.8927 0.8058 -0.2155 0.1654 Uiso calc . 1.00 H
H7* 0.3995 0.7679 0.1428 0.0830 Uiso calc P 0.34 H
H8* 0.4279 0.8707 0.0768 0.0742 Uiso calc P 0.34 H
H10* 0.5423 0.2725 0.0793 0.0713 Uiso calc P 0.34 H
H11* 0.5198 0.1894 0.1429 0.0818 Uiso calc P 0.34 H
H12* 0.5078 0.8140 0.0220 0.0605 Uiso calc P 0.34 H
H13* 0.5627 0.3151 0.0216 0.0536 Uiso calc P 0.34 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 . . 117.2(3) ?
C20 O4 C24 . . 118.4(3) ?
C14 N5 C15 . . 121.6(3) ?
C14 N5 H5 . . 119.3 no
C15 N5 H5 . . 119.2 no
Cl C6 C7 . . 125.0(10) ?
Cl C6 C11 . . 111.0(10) ?
C7 C6 C11 . . 123.0(10) ?
C6 C7 C8 . . 119.0(10) ?
C6 C7 H7 . . 120.4 no
C8 C7 H7 . . 120.4 no
C7 C8 C9 . . 122.2(10) ?
C7 C8 H8 . . 119.4 no
C9 C8 H8 . . 118.4 no
C8 C9 C10 . . 119.5(8) ?
C8 C9 C12 . . 118.7(8) ?
C10 C9 C12 . . 121.4(7) ?
C9 C10 C11 . . 120.4(8) ?
C9 C10 H10 . . 120.3 no
C11 C10 H10 . . 119.3 no
C6 C11 C10 . . 114.0(10) ?
C6 C11 H11 . . 123.1 no
C10 C11 H11 . . 122.0 no
C9 C12 C13 . . 126.4(6) yes
C9 C12 H12 . . 116.7 no
C13 C12 H12 . . 116.9 no
C12 C13 C14 . . 121.3(6) yes
C12 C13 H13 . . 119.3 no
C14 C13 H13 . . 119.4 no
O2 C14 N5 . . 124.1(3) ?
O2 C14 C13 . . 119.2(4) ?
N5 C14 C13 . . 114.0(4) ?
N5 C15 C16 . . 113.6(3) ?
N5 C15 H15A . . 108.5 no
N5 C15 H15B . . 108.4 no
C16 C15 H15A . . 108.4 no
C16 C15 H15B . . 108.5 no
H15A C15 H15B . . 109.4 no
C15 C16 C17 . . 115.0(3) ?
C15 C16 H16A . . 108.1 no
C15 C16 H16B . . 108.2 no
C17 C16 H16A . . 108.0 no
C17 C16 H16B . . 108.1 no
H16A C16 H16B . . 109.4 no
C16 C17 C18 . . 120.3(4) ?
C16 C17 C22 . . 121.7(4) ?
C18 C17 C22 . . 118.0(4) ?
C17 C18 C19 . . 121.5(4) ?
C17 C18 H18 . . 119.3 no
C19 C18 H18 . . 119.2 no
O3 C19 C18 . . 124.9(4) ?
O3 C19 C20 . . 115.9(4) ?
C18 C19 C20 . . 119.2(4) ?
O4 C20 C19 . . 115.1(4) ?
O4 C20 C21 . . 124.9(4) ?
C19 C20 C21 . . 120.1(4) ?
C20 C21 C22 . . 119.9(4) ?
C20 C21 H21 . . 120.1 no
C22 C21 H21 . . 120.1 no
C17 C22 C21 . . 121.4(4) ?
C17 C22 H22 . . 119.3 no
C21 C22 H22 . . 119.3 no
O3 C23 H23A . . 109.5 no
O3 C23 H23B . . 109.5 no
O3 C23 H23C . . 109.5 no
H23A C23 H23B . . 109.5 no
H23A C23 H23C . . 109.5 no
H23B C23 H23C . . 109.4 no
O4 C24 H24A . . 109.5 no
O4 C24 H24B . . 109.5 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* . . 116(2) ?
Cl* C6* C11* . . 130(2) ?
C7* C6* C11* . . 113(2) ?
C6* C7* C8* . . 120(2) ?
C6* C7* H7* . . 119.8 no
C8* C7* H7* . . 119.3 no
C7* C8* C9* . . 122.0(10) ?
C7* C8* H8* . . 116.8 no
C9* C8* H8* . . 120.6 no
C8* C9* C10* . . 113.0(10) ?
C8* C9* C12* . . 121.0(10) ?
C10* C9* C12* . . 125.2(10) ?
C9* C10* C11* . . 124.0(10) ?
C9* C10* H10* . . 117.3 no
C11* C10* H10* . . 118.5 no
C6* C11* C10* . . 125.0(10) ?
C6* C11* H11* . . 115.7 no
C10* C11* H11* . . 118.7 no
C9* C12* C13* . . 119.2(8) ?
C9* C12* C13* . 3_665 118.9(8) ?
C9* C12* H12* . . 108.9 no
C13* C12* C13* . 3_665 90.8(7) ?
C13* C12* H12* . . 108.9 no
C13* C12* H12* 3_665 . 108.7 no
C14 C13* C12* . . 115.6(6) ?
C14 C13* C12* . 3_665 120.8(7) ?
C14 C13* H13* . . 109.8 no
C12* C13* C12* . 3_665 89.2(7) ?
C12* C13* H13* . . 109.8 no
C12* C13* H13* 3_665 . 110.0 no
C9* C12* C13* . 3_665 118.9(8) yes
C13* C12* C13* . 3_665 90.8(7) yes
H12* C12* C13* . 3_665 108.7 no
C12* C13* C12* . 3_665 89.2(8) yes
H13* C13* C12* . 3_665 110.0 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 . 1.72(2) yes
O2 C14 . 1.205(5) ?
O3 C19 . 1.354(5) ?
O3 C23 . 1.424(5) ?
O4 C20 . 1.365(5) ?
O4 C24 . 1.407(5) ?
N5 C14 . 1.325(5) ?
N5 C15 . 1.449(4) ?
N5 H5 . 0.950 no
C6 C7 . 1.38(2) ?
C6 C11 . 1.42(2) ?
C7 C8 . 1.32(2) ?
C7 H7 . 0.951 no
C8 C9 . 1.420(10) ?
C8 H8 . 0.945 no
C9 C10 . 1.380(10) ?
C9 C12 . 1.450(10) ?
C10 C11 . 1.460(10) ?
C10 H10 . 0.954 no
C11 H11 . 0.942 no
C12 C13 . 1.330(10) yes
C12 H12 . 0.950 no
C13 C14 . 1.401(8) ?
C13 H13 . 0.950 no
C14 C13* . 1.770(10) ?
C15 C16 . 1.454(5) ?
C15 H15A . 0.950 no
C15 H15B . 0.951 no
C16 C17 . 1.510(6) ?
C16 H16A . 0.952 no
C16 H16B . 0.949 no
C17 C18 . 1.391(6) ?
C17 C22 . 1.365(6) ?
C18 C19 . 1.380(6) ?
C18 H18 . 0.950 no
C19 C20 . 1.389(6) ?
C20 C21 . 1.362(6) ?
C21 C22 . 1.396(6) ?
C21 H21 . 0.949 no
C22 H22 . 0.949 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* . 1.76(3) yes
C6* C7* . 1.28(4) ?
C6* C11* . 1.31(3) ?
C7* C8* . 1.48(3) ?
C7* H7* . 0.947 no
C8* C9* . 1.28(2) ?
C8* H8* . 0.940 no
C9* C10* . 1.32(2) ?
C9* C12* . 1.530(10) ?
C10* C11* . 1.32(2) ?
C10* H10* . 0.942 no
C11* H11* . 0.973 no
C12* C13* . 1.530(10) yes
C12* C13* 3_665 1.530(10) yes
C12* H12* . 0.951 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 2.14 3.013(3) 152 yes
