#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/80/7208044.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_7208044
loop_
_publ_author_name
'Choi, Eun-Young'
'Jazbinsek, Mojca'
'Lee, Seung-Heon'
'Günter, Peter'
'Yun, Hoseop'
'Lee, Soon W.'
'Kwon, O-Pil'
_publ_section_title
;
 Co-crystal structure selection of nonlinear optical analogue polyenes
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              4306
_journal_paper_doi               10.1039/c2ce06057d
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C18.5 H17 N2 O'
_chemical_formula_weight         282.84
_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                 95.397(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.050(3)
_cell_length_b                   14.200(3)
_cell_length_c                   10.068(2)
_cell_measurement_reflns_used    11296
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.34
_cell_volume                     1572.8(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1357
_diffrn_reflns_av_sigmaI/netI    0.1011
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11305
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'not measured'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   7(3)
_refine_ls_extinction_coef       0.0013(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1835
_refine_ls_R_factor_gt           0.0664
_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)+(0.0629P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1798
_reflns_number_gt                1449
_reflns_number_total             3518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06057d.txt
_cod_data_source_block           2cc
_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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1572.6(6)
_cod_original_sg_symbol_H-M      'Cc '
_cod_original_formula_sum        'C18.50 H17 N2 O'
_cod_database_code               7208044
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
O1 O 0.7067(4) 0.5746(3) 0.7523(3) 0.1236(15) Uani 1 1 d .
N1 N 0.2908(4) 0.7947(3) -0.5394(4) 0.1029(14) Uani 1 1 d .
N2 N 0.3293(5) 0.5271(4) -0.3246(5) 0.1255(17) Uani 1 1 d .
C1 C 0.6709(4) 0.6182(4) 0.6345(4) 0.0806(14) Uani 1 1 d .
C2 C 0.6200(4) 0.5622(3) 0.5318(4) 0.0923(15) Uani 1 1 d .
H2 H 0.6123 0.4977 0.5446 0.111 Uiso 1 1 calc R
C3 C 0.6841(4) 0.7124(4) 0.6159(4) 0.0717(12) Uani 1 1 d .
H3 H 0.7180 0.7501 0.6852 0.086 Uiso 1 1 calc R
C4 C 0.5808(4) 0.6020(4) 0.4106(4) 0.0819(14) Uani 1 1 d .
H4 H 0.5451 0.5640 0.3425 0.098 Uiso 1 1 calc R
C5 C 0.6467(4) 0.7514(3) 0.4935(4) 0.0712(12) Uani 1 1 d .
H5 H 0.6573 0.8156 0.4807 0.085 Uiso 1 1 calc R
C6 C 0.5936(3) 0.6974(3) 0.3885(3) 0.0611(12) Uani 1 1 d .
C7 C 0.5585(3) 0.7428(3) 0.2618(3) 0.0666(12) Uani 1 1 d .
H7 H 0.5683 0.8079 0.2605 0.080 Uiso 1 1 calc R
C8 C 0.5136(4) 0.7037(3) 0.1459(4) 0.0684(11) Uani 1 1 d .
H8 H 0.5003 0.6390 0.1449 0.082 Uiso 1 1 calc R
C9 C 0.4848(4) 0.7545(3) 0.0233(4) 0.0635(11) Uani 1 1 d .
C10 C 0.4992(4) 0.8578(3) 0.0212(4) 0.0792(13) Uani 1 1 d .
H10A H 0.5736 0.8741 0.0754 0.095 Uiso 1 1 calc R
H10B H 0.4322 0.8860 0.0625 0.095 Uiso 1 1 calc R
C11 C 0.4399(3) 0.7072(3) -0.0888(3) 0.0642(11) Uani 1 1 d .
H11 H 0.4324 0.6421 -0.0852 0.077 Uiso 1 1 calc R
C12 C 0.5037(6) 0.8998(4) -0.1130(5) 0.116(2) Uani 1 1 d .
C13 C 0.4106(5) 0.8585(4) -0.2150(5) 0.0998(17) Uani 1 1 d .
H13A H 0.3314 0.8840 -0.2008 0.120 Uiso 1 1 calc R
H13B H 0.4294 0.8777 -0.3031 0.120 Uiso 1 1 calc R
C14 C 0.4041(3) 0.7545(3) -0.2107(4) 0.0645(12) Uani 1 1 d .
C15 C 0.4981(10) 1.0052(5) -0.1092(7) 0.215(5) Uani 1 1 d .
H15A H 0.4239 1.0245 -0.0745 0.323 Uiso 1 1 calc R
H15B H 0.5004 1.0297 -0.1978 0.323 Uiso 1 1 calc R
H15C H 0.5662 1.0290 -0.0529 0.323 Uiso 1 1 calc R
C16 C 0.6143(11) 0.8968(9) -0.1599(9) 0.109(4) Uani 0.50 1 d P
H16A H 0.6096 0.9246 -0.2471 0.164 Uiso 0.50 1 calc PR
H16B H 0.6402 0.8325 -0.1650 0.164 Uiso 0.50 1 calc PR
H16C H 0.6716 0.9311 -0.1008 0.164 Uiso 0.50 1 calc PR
C17 C 0.3582(3) 0.7063(4) -0.3224(3) 0.0730(14) Uani 1 1 d .
C18 C 0.3219(4) 0.7543(4) -0.4439(4) 0.0794(14) Uani 1 1 d .
C19 C 0.3433(5) 0.6073(5) -0.3247(5) 0.0880(15) Uani 1 1 d .
H1O H 0.725(5) 0.627(4) 0.813(6) 0.13(2) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C1 O1 H1O 103(3)
C3 C1 O1 122.7(4)
C3 C1 C2 120.3(4)
O1 C1 C2 117.0(5)
C4 C2 C1 120.0(4)
C4 C2 H2 120.0
C1 C2 H2 120.0
C1 C3 C5 119.4(4)
C1 C3 H3 120.3
C5 C3 H3 120.3
C2 C4 C6 121.0(4)
C2 C4 H4 119.5
C6 C4 H4 119.5
C3 C5 C6 121.9(4)
C3 C5 H5 119.1
C6 C5 H5 119.1
C4 C6 C5 117.4(4)
C4 C6 C7 123.7(4)
C5 C6 C7 118.8(4)
C8 C7 C6 128.7(4)
C8 C7 H7 115.6
C6 C7 H7 115.6
C7 C8 C9 124.8(4)
C7 C8 H8 117.6
C9 C8 H8 117.6
C11 C9 C8 119.7(4)
C11 C9 C10 120.6(4)
C8 C9 C10 119.6(3)
C9 C10 C12 115.2(4)
C9 C10 H10A 108.5
C12 C10 H10A 108.5
C9 C10 H10B 108.5
C12 C10 H10B 108.5
H10A C10 H10B 107.5
C9 C11 C14 122.0(4)
C9 C11 H11 119.0
C14 C11 H11 119.0
C16 C12 C10 114.5(6)
C16 C12 C15 94.7(7)
C10 C12 C15 112.0(5)
C16 C12 C13 109.4(6)
C10 C12 C13 112.7(5)
C15 C12 C13 112.3(5)
C14 C13 C12 113.7(4)
C14 C13 H13A 108.8
C12 C13 H13A 108.8
C14 C13 H13B 108.8
C12 C13 H13B 108.8
H13A C13 H13B 107.7
C17 C14 C11 121.5(4)
C17 C14 C13 119.3(4)
C11 C14 C13 119.1(4)
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C12 C16 H16A 109.5
C12 C16 H16B 109.5
H16A C16 H16B 109.5
C12 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C14 C17 C19 122.9(4)
C14 C17 C18 121.2(5)
C19 C17 C18 116.0(4)
N1 C18 C17 177.9(6)
N2 C19 C17 178.5(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.363(5)
O1 H1O 0.97(6)
N1 C18 1.144(5)
N2 C19 1.149(7)
C1 C3 1.360(6)
C1 C2 1.380(6)
C2 C4 1.377(6)
C2 H2 0.9300
C3 C5 1.379(5)
C3 H3 0.9300
C4 C6 1.382(5)
C4 H4 0.9300
C5 C6 1.390(6)
C5 H5 0.9300
C6 C7 1.450(5)
C7 C8 1.344(5)
C7 H7 0.9300
C8 C9 1.440(5)
C8 H8 0.9300
C9 C11 1.365(5)
C9 C10 1.476(6)
C10 C12 1.482(6)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C14 1.422(5)
C11 H11 0.9300
C12 C16 1.351(12)
C12 C15 1.498(9)
C12 C13 1.503(6)
C13 C14 1.478(6)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C17 1.373(5)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 C19 1.415(8)
C17 C18 1.425(6)
