#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103826.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_2103826
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                 91.290(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.180(4)
_cell_length_b                   4.9770(12)
_cell_length_c                   33.642(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      11.8
_cell_measurement_theta_min      10.1
_cell_volume                     3545.4(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  0.017
_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            5109
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        2.13
_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    1.296
_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         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4089
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.0040
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0787P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2010
_reflns_number_gt                1078
_reflns_number_total             4089
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm0063.cif
_cod_data_source_block           If
_cod_original_cell_volume        3545.3(11)
_cod_original_formula_sum        'C19 H20 Cl N O3 '
_cod_database_code               2103826
_cod_database_fobs_code          2103826
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 0.4138(3) 0.459(2) 0.1908(2) 0.187(2) Uani d P 0.71 Cl
Cl* 0.4252(7) 0.425(4) 0.1980(2) 0.154(4) Uani d P 0.29 Cl
O2 0.6220(2) 0.8840(6) -0.01682(8) 0.1290(10) Uani d . 1.00 O
O3 0.7839(2) 0.0712(7) -0.20320(10) 0.1200(10) Uani d . 1.00 O
O4 0.87320(10) 0.4161(6) -0.21004(8) 0.1210(10) Uani d . 1.00 O
N5 0.6568(2) 0.4624(6) -0.02576(8) 0.0903(10) Uani d . 1.00 N
C6 0.4468(8) 0.531(4) 0.1467(5) 0.123(7) Uani d P 0.71 C
C6* 0.459(2) 0.486(7) 0.1509(7) 0.0607 Uani d P 0.29 C
C7 0.4285(6) 0.747(2) 0.1223(4) 0.118(5) Uani d P 0.71 C
C7* 0.4340(10) 0.670(6) 0.1317(8) 0.0691 Uani d P 0.29 C
C8 0.4627(5) 0.798(3) 0.0899(4) 0.126(3) Uani d P 0.71 C
C8* 0.4458(10) 0.735(4) 0.0889(6) 0.0619 Uani d P 0.29 C
C9 0.5137(4) 0.639(2) 0.0789(2) 0.088(2) Uani d P 0.71 C
C9* 0.4877(6) 0.578(3) 0.0698(4) 0.0443 Uani d P 0.29 C
C10 0.5338(4) 0.442(2) 0.1043(3) 0.111(2) Uani d P 0.71 C
C10* 0.5143(7) 0.379(3) 0.0910(4) 0.0594 Uani d P 0.29 C
C11 0.5010(10) 0.384(4) 0.1378(6) 0.156(5) Uani d P 0.71 C
C11* 0.498(2) 0.339(6) 0.1333(9) 0.0682 Uani d P 0.29 C
C12 0.5480(4) 0.7090(10) 0.0432(2) 0.097(2) Uani d P 0.71 C
C12* 0.4998(6) 0.629(2) 0.0257(3) 0.048(4) Uani d P 0.29 C
C13 0.5899(4) 0.5560(10) 0.0249(2) 0.090(2) Uani d P 0.71 C
C13* 0.5486(6) 0.459(2) 0.0041(3) 0.054(4) Uani d P 0.29 C
C14 0.6201(2) 0.6470(10) -0.00950(10) 0.1010(10) Uani d . 1.00 C
C15 0.6989(2) 0.5327(7) -0.05760(10) 0.1060(10) Uani d . 1.00 C
C16 0.7477(2) 0.3320(10) -0.06360(10) 0.134(2) Uani d . 1.00 C
C17 0.7817(2) 0.3580(10) -0.10260(10) 0.1030(10) Uani d . 1.00 C
C18 0.7661(2) 0.1973(9) -0.1350(2) 0.1000(10) Uani d . 1.00 C
C19 0.7963(2) 0.2197(9) -0.17040(10) 0.0920(10) Uani d . 1.00 C
C20 0.8447(2) 0.4110(10) -0.17390(10) 0.0970(10) Uani d . 1.00 C
C21 0.8598(2) 0.5739(9) -0.1429(2) 0.1090(10) Uani d . 1.00 C
C22 0.8282(2) 0.5470(10) -0.10680(10) 0.1150(10) Uani d . 1.00 C
C23 0.7292(2) -0.0950(10) -0.20250(10) 0.136(2) Uani d . 1.00 C
C24 0.9155(2) 0.6290(10) -0.21750(10) 0.141(2) Uani d . 1.00 C
H5 0.6555 0.2821 -0.0165 0.1082 Uiso calc . 1.00 H
H7 0.3930 0.8544 0.1285 0.1427 Uiso calc P 0.71 H
H8 0.4514 0.9468 0.0737 0.1524 Uiso calc P 0.71 H
H10 0.5710 0.3428 0.0988 0.1337 Uiso calc P 0.71 H
H11 0.5140 0.2437 0.1552 0.1870 Uiso calc P 0.71 H
H12 0.5396 0.8810 0.0319 0.1168 Uiso calc P 0.71 H
H13 0.5995 0.3827 0.0352 0.1083 Uiso calc P 0.71 H
H15A 0.7186 0.6993 -0.0513 0.1273 Uiso calc . 1.00 H
H15B 0.6747 0.5508 -0.0816 0.1273 Uiso calc . 1.00 H
H16A 0.7287 0.1593 -0.0627 0.1602 Uiso calc . 1.00 H
H16B 0.7781 0.3474 -0.0425 0.1602 Uiso calc . 1.00 H
H18 0.7335 0.0675 -0.1325 0.1203 Uiso calc . 1.00 H
H21 0.8917 0.7067 -0.1455 0.1309 Uiso calc . 1.00 H
H22 0.8393 0.6604 -0.0850 0.1379 Uiso calc . 1.00 H
H23A 0.6929 0.0134 -0.1990 0.1636 Uiso calc . 1.00 H
H23B 0.7332 -0.2193 -0.1811 0.1636 Uiso calc . 1.00 H
H23C 0.7252 -0.1901 -0.2269 0.1636 Uiso calc . 1.00 H
H24A 0.9317 0.6109 -0.2434 0.1697 Uiso calc . 1.00 H
H24B 0.9493 0.6242 -0.1984 0.1697 Uiso calc . 1.00 H
H24C 0.8938 0.7956 -0.2155 0.1697 Uiso calc . 1.00 H
H7* 0.4046 0.7813 0.1452 0.0830 Uiso calc P 0.29 H
H8* 0.4247 0.8813 0.0758 0.0743 Uiso calc P 0.29 H
H10* 0.5437 0.2634 0.0789 0.0713 Uiso calc P 0.29 H
H11* 0.5188 0.1960 0.1472 0.0818 Uiso calc P 0.29 H
H12* 0.5089 0.8138 0.0218 0.0586 Uiso calc P 0.29 H
H13* 0.5604 0.3101 0.0203 0.0647 Uiso calc P 0.29 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 . . 116.7(4) ?
C20 O4 C24 . . 117.7(4) ?
C14 N5 C15 . . 120.9(3) ?
C14 N5 H5 . . 119.6 no
C15 N5 H5 . . 119.6 no
Cl C6 C7 . . 124.0(10) ?
Cl C6 C11 . . 115.0(10) ?
C7 C6 C11 . . 119.0(10) ?
C6 C7 C8 . . 118.0(10) ?
C6 C7 H7 . . 121.0 no
C8 C7 H7 . . 120.9 no
C7 C8 C9 . . 122.0(10) ?
C7 C8 H8 . . 118.7 no
C9 C8 H8 . . 118.4 no
C8 C9 C10 . . 118.2(9) ?
C8 C9 C12 . . 119.1(8) ?
C10 C9 C12 . . 122.2(7) ?
C9 C10 C11 . . 120.0(10) ?
C9 C10 H10 . . 120.0 no
C11 C10 H10 . . 119.5 no
C6 C11 C10 . . 120.0(10) ?
C6 C11 H11 . . 119.4 no
C10 C11 H11 . . 120.6 no
C9 C12 C13 . . 126.3(6) yes
C9 C12 H12 . . 116.9 no
C13 C12 H12 . . 116.8 no
C12 C13 C14 . . 121.0(6) yes
C12 C13 H13 . . 119.5 no
C14 C13 H13 . . 119.5 no
O2 C14 N5 . . 124.6(4) ?
O2 C14 C13 . . 119.9(5) ?
N5 C14 C13 . . 113.5(5) ?
N5 C15 C16 . . 112.7(3) ?
N5 C15 H15A . . 108.6 no
N5 C15 H15B . . 108.7 no
C16 C15 H15A . . 108.7 no
C16 C15 H15B . . 108.7 no
H15A C15 H15B . . 109.4 no
C15 C16 C17 . . 114.3(4) ?
C15 C16 H16A . . 108.3 no
C15 C16 H16B . . 108.2 no
C17 C16 H16A . . 108.3 no
C17 C16 H16B . . 108.2 no
H16A C16 H16B . . 109.5 no
C16 C17 C18 . . 121.5(4) ?
C16 C17 C22 . . 120.3(4) ?
C18 C17 C22 . . 118.2(4) ?
C17 C18 C19 . . 122.0(4) ?
C17 C18 H18 . . 119.0 no
C19 C18 H18 . . 119.0 no
O3 C19 C18 . . 125.5(4) ?
O3 C19 C20 . . 115.5(4) ?
C18 C19 C20 . . 119.0(4) ?
O4 C20 C19 . . 115.2(4) ?
O4 C20 C21 . . 124.9(4) ?
C19 C20 C21 . . 119.9(4) ?
C20 C21 C22 . . 120.1(4) ?
C20 C21 H21 . . 120.0 no
C22 C21 H21 . . 119.9 no
C17 C22 C21 . . 120.8(4) ?
C17 C22 H22 . . 119.6 no
C21 C22 H22 . . 119.7 no
O3 C23 H23A . . 109.4 no
O3 C23 H23B . . 109.4 no
O3 C23 H23C . . 109.4 no
H23A C23 H23B . . 109.5 no
H23A C23 H23C . . 109.6 no
H23B C23 H23C . . 109.5 no
O4 C24 H24A . . 109.5 no
O4 C24 H24B . . 109.5 no
O4 C24 H24C . . 109.4 no
H24A C24 H24B . . 109.5 no
H24A C24 H24C . . 109.5 no
H24B C24 H24C . . 109.4 no
Cl* C6* C7* . . 114(2) ?
Cl* C6* C11* . . 126(2) ?
C7* C6* C11* . . 117(2) ?
C6* C7* C8* . . 125(2) ?
C6* C7* H7* . . 117.4 no
C8* C7* H7* . . 117.1 no
C7* C8* C9* . . 117.0(10) ?
C7* C8* H8* . . 121.2 no
C9* C8* H8* . . 121.6 no
C8* C9* C10* . . 116.0(10) ?
C8* C9* C12* . . 119.0(10) ?
C10* C9* C12* . . 124.0(10) ?
C9* C10* C11* . . 120.0(10) ?
C9* C10* H10* . . 119.5 no
C11* C10* H10* . . 119.7 no
C6* C11* C10* . . 122(2) ?
C6* C11* H11* . . 119.7 no
C10* C11* H11* . . 117.9 no
C9* C12* C13* . . 119.9(9) ?
C9* C12* C13* . 3_665 118.0(10) yes
C9* C12* H12* . . 109.5 no
C13* C12* C13* . 3_665 88.8(9) yes
C13* C12* H12* . . 109.2 no
C13* C12* H12* 3_665 . 109.2 no
C12* C13* C12* . 3_665 91.2(9) yes
C12* C13* H13* . . 109.2 no
C12* C13* H13* 3_665 . 109.2 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 . 1.69(2) yes
O2 C14 . 1.207(6) ?
O3 C19 . 1.349(6) ?
O3 C23 . 1.423(6) ?
O4 C20 . 1.369(5) ?
O4 C24 . 1.413(6) ?
N5 C14 . 1.329(6) ?
N5 C15 . 1.452(5) ?
N5 H5 . 0.951 no
C6 C7 . 1.40(2) ?
C6 C11 . 1.39(3) ?
C7 C8 . 1.35(2) ?
C7 H7 . 0.949 no
C8 C9 . 1.390(10) ?
C8 H8 . 0.948 no
C9 C10 . 1.370(10) ?
C9 C12 . 1.460(10) ?
C10 C11 . 1.37(2) ?
C10 H10 . 0.951 no
C11 H11 . 0.951 no
C12 C13 . 1.330(10) yes
C12 H12 . 0.950 no
C13 C14 . 1.409(8) ?
C13 H13 . 0.950 no
C15 C16 . 1.455(7) ?
C15 H15A . 0.950 no
C15 H15B . 0.951 no
C16 C17 . 1.517(7) ?
C16 H16A . 0.949 no
C16 H16B . 0.950 no
C17 C18 . 1.386(7) ?
C17 C22 . 1.371(7) ?
C18 C19 . 1.368(7) ?
C18 H18 . 0.951 no
C19 C20 . 1.406(7) ?
C20 C21 . 1.355(7) ?
C21 C22 . 1.406(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 . 0.949 no
C24 H24B . 0.950 no
C24 H24C . 0.951 no
Cl* C6* . 1.78(3) yes
C6* C7* . 1.23(4) ?
C6* C11* . 1.27(5) ?
C7* C8* . 1.50(4) ?
C7* H7* . 0.955 no
C8* C9* . 1.35(2) ?
C8* H8* . 0.957 no
C9* C10* . 1.34(2) ?
C9* C12* . 1.53(2) ?
C10* C11* . 1.48(3) ?
C10* H10* . 0.949 no
C11* H11* . 0.949 no
C12* C13* . 1.53(2) yes
C12* C13* 3_665 1.48(2) yes
C12* H12* . 0.950 no
C13* H13* . 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 2.10 2.989(4) 154 yes
