#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:30:31 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179582 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/47/4504777.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4504777
loop_
_publ_author_name
'Chowdhury, Masrur'
'Kariuki, Benson M.'
_publ_section_title
;
 Supramolecular Assembly in Cinnamate Structures:  The Influence of
 the Ammonium Ion and Halogen Interactions
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              774
_journal_paper_doi               10.1021/cg050604k
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C9 H6 Br O2, H4 N'
_chemical_formula_sum            'C9 H10 Br N O2'
_chemical_formula_weight         244.09
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.411(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   42.7088(15)
_cell_length_b                   4.0066(2)
_cell_length_c                   11.6089(6)
_cell_measurement_reflns_used    2944
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.40
_cell_measurement_theta_min      4.14
_cell_volume                     1986.43(16)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5888
_diffrn_reflns_theta_full        70.40
_diffrn_reflns_theta_max         70.40
_diffrn_reflns_theta_min         4.14
_exptl_absorpt_coefficient_mu    5.395
_exptl_absorpt_correction_T_max  0.4983
_exptl_absorpt_correction_T_min  0.4117
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+8.2708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2944
_reflns_number_total             3113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050604ksi20051114_115359.cif
_cod_data_source_block           mc1b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4504777
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.18098(15) 0.2022(16) 0.6206(5) 0.0403(14) Uani 1 1 d .
C2 C 0.15529(15) 0.1164(16) 0.6880(6) 0.0437(15) Uani 1 1 d .
H2 H 0.1585 0.0140 0.7590 0.052 Uiso 1 1 calc R
C3 C 0.12517(16) 0.1827(15) 0.6500(6) 0.0430(14) Uani 1 1 d .
C4 C 0.11943(17) 0.3407(17) 0.5472(6) 0.0513(16) Uani 1 1 d .
H4 H 0.0991 0.3876 0.5233 0.062 Uiso 1 1 calc R
C5 C 0.1449(2) 0.429(2) 0.4795(6) 0.058(2) Uani 1 1 d .
H5 H 0.1415 0.5372 0.4097 0.070 Uiso 1 1 calc R
C6 C 0.17508(17) 0.3585(16) 0.5144(6) 0.0480(16) Uani 1 1 d .
H6 H 0.1917 0.4151 0.4670 0.058 Uiso 1 1 calc R
C7 C 0.21321(16) 0.1453(16) 0.6579(6) 0.0451(15) Uani 1 1 d .
H7 H 0.2287 0.1688 0.6026 0.054 Uiso 1 1 calc R
C8 C 0.22246(19) 0.063(2) 0.7634(7) 0.0496(19) Uani 1 1 d .
H8 H 0.2073 0.0349 0.8196 0.059 Uiso 1 1 calc R
C9 C 0.25637(16) 0.0132(16) 0.7969(6) 0.0424(14) Uani 1 1 d .
C10 C -0.05484(14) -0.2007(14) 0.3734(5) 0.0355(13) Uani 1 1 d .
C11 C -0.02934(14) -0.1232(15) 0.4418(5) 0.0385(13) Uani 1 1 d .
H11 H -0.0322 -0.0159 0.5120 0.046 Uiso 1 1 calc R
C12 C 0.00011(14) -0.2048(16) 0.4060(5) 0.0409(14) Uani 1 1 d .
C13 C 0.00545(18) -0.3543(18) 0.3027(6) 0.0537(17) Uani 1 1 d .
H13 H 0.0257 -0.4030 0.2792 0.064 Uiso 1 1 calc R
C14 C -0.02002(19) -0.4318(19) 0.2335(6) 0.0525(18) Uani 1 1 d .
H14 H -0.0168 -0.5358 0.1629 0.063 Uiso 1 1 calc R
C15 C -0.04999(17) -0.3576(18) 0.2674(6) 0.0489(16) Uani 1 1 d .
H15 H -0.0669 -0.4114 0.2202 0.059 Uiso 1 1 calc R
C16 C -0.08722(15) -0.1335(16) 0.4100(6) 0.0445(15) Uani 1 1 d .
H16 H -0.1024 -0.1261 0.3521 0.053 Uiso 1 1 calc R
C17 C -0.09704(18) -0.0828(17) 0.5157(6) 0.0427(17) Uani 1 1 d .
H17 H -0.0821 -0.0915 0.5742 0.051 Uiso 1 1 calc R
C18 C -0.12990(16) -0.0129(16) 0.5505(6) 0.0437(15) Uani 1 1 d .
O1 O 0.27698(13) 0.0386(15) 0.7204(4) 0.0613(15) Uani 1 1 d .
O2 O 0.26171(13) -0.0443(14) 0.8998(4) 0.0617(14) Uani 1 1 d .
O3 O -0.15089(12) -0.0138(15) 0.4728(4) 0.0577(14) Uani 1 1 d .
O4 O -0.13524(12) 0.0291(15) 0.6547(4) 0.0624(14) Uani 1 1 d .
Br1 Br 0.091337(17) 0.0529(3) 0.74557(5) 0.0674(3) Uani 1 1 d .
Br2 Br 0.034944(17) -0.0941(2) 0.50281(5) 0.0605(2) Uani 1 1 d .
N1 N 0.28801(15) 0.5446(17) 0.5440(7) 0.0662(18) Uani 1 1 d D
H1N H 0.2855(16) 0.712(12) 0.598(4) 0.099 Uiso 1 1 d D
H2N H 0.2806(15) 0.348(9) 0.573(5) 0.099 Uiso 1 1 d D
H3N H 0.3090(5) 0.527(17) 0.527(6) 0.099 Uiso 1 1 d D
H4N H 0.2770(15) 0.603(16) 0.478(4) 0.099 Uiso 1 1 d D
N2 N -0.16133(15) 0.5110(18) 0.7983(7) 0.070(2) Uani 1 1 d D
H5N H -0.1484(14) 0.511(17) 0.735(4) 0.105 Uiso 1 1 d D
H6N H -0.1534(15) 0.655(14) 0.853(4) 0.105 Uiso 1 1 d D
H7N H -0.1619(17) 0.298(7) 0.829(6) 0.105 Uiso 1 1 d D
H8N H -0.1811(7) 0.576(17) 0.777(6) 0.105 Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables 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
C2 C1 C6 117.8(6)
C2 C1 C7 122.6(6)
C6 C1 C7 119.6(6)
C3 C2 C1 120.5(6)
C4 C3 C2 121.8(6)
C4 C3 Br1 120.2(5)
C2 C3 Br1 118.1(5)
C3 C4 C5 118.2(7)
C6 C5 C4 121.1(7)
C5 C6 C1 120.7(7)
C8 C7 C1 126.0(6)
C7 C8 C9 123.3(7)
O2 C9 O1 124.9(6)
O2 C9 C8 116.3(6)
O1 C9 C8 118.8(6)
C11 C10 C15 119.1(6)
C11 C10 C16 122.1(5)
C15 C10 C16 118.7(6)
C12 C11 C10 119.7(6)
C13 C12 C11 122.2(6)
C13 C12 Br2 119.1(5)
C11 C12 Br2 118.7(5)
C12 C13 C14 118.3(7)
C15 C14 C13 121.0(7)
C14 C15 C10 119.6(7)
C17 C16 C10 127.1(6)
C16 C17 C18 126.1(7)
O4 C18 O3 124.0(6)
O4 C18 C17 117.9(6)
O3 C18 C17 118.0(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.395(9)
C1 C6 1.404(9)
C1 C7 1.458(9)
C2 C3 1.383(9)
C3 C4 1.372(10)
C3 Br1 1.901(7)
C4 C5 1.392(12)
C5 C6 1.377(11)
C7 C8 1.325(10)
C8 C9 1.510(10)
C9 O2 1.237(8)
C9 O1 1.259(8)
C10 C11 1.379(8)
C10 C15 1.398(9)
C10 C16 1.474(9)
C11 C12 1.367(8)
C12 C13 1.362(9)
C12 Br2 1.910(6)
C13 C14 1.382(11)
C14 C15 1.375(11)
C16 C17 1.315(10)
C17 C18 1.490(10)
C18 O4 1.244(8)
C18 O3 1.267(8)
