#------------------------------------------------------------------------------
#$Date: 2016-02-17 15:50:08 +0200 (Wed, 17 Feb 2016) $
#$Revision: 176614 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/74/2107478.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_2107478
loop_
_publ_author_name
'Lorenzo, Daniel A.'
'Forrest, Sebastian J. K.'
'Sparkes, Hazel A.'
_publ_section_title
;
 Crystal engineering: co-crystals of cinnamic acid derivatives with a
 pyridyl derivative co-crystallizer
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              87
_journal_page_last               95
_journal_paper_doi               10.1107/S2052520615019678
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'C11 H12 O4, C6 H6 N2 O'
_chemical_formula_sum            'C17 H18 N2 O5'
_chemical_formula_weight         330.33
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.975(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0200(8)
_cell_length_b                   9.8795(5)
_cell_length_c                   11.6434(6)
_cell_measurement_reflns_used    1157
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.53
_cell_volume                     1600.80(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14321
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.112
_diffrn_reflns_theta_min         1.463
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0619 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.9013.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0556P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                2262
_reflns_number_total             3896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bm5077sup1.cif
_cod_data_source_block           4B
_cod_depositor_comments
;Adding full bibliography for 2107471--2107478.cif.

 Adding full bibliography for 2107471--2107478.cif.
;
_cod_database_code               2107478
_cod_database_fobs_code          2107478
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
O O1 0.70928(12) 0.44610(14) 0.25409(14) 0.0243(4) Uani d 1
H H1 0.684(2) 0.452(3) 0.1701(7) 0.073(11) Uiso d 1
O O2 0.64521(11) 0.65394(15) 0.24844(14) 0.0265(4) Uani d 1
O O3 0.88680(11) 0.47245(14) 0.97075(13) 0.0237(4) Uani d 1
O O4 0.91711(11) 0.26152(14) 0.84940(14) 0.0267(4) Uani d 1
C C1 0.78704(15) 0.5964(2) 0.6831(2) 0.0206(5) Uani d 1
H H1A 0.7563 0.6742 0.6477 0.025 Uiso calc 1
C C2 0.81427(15) 0.5959(2) 0.8012(2) 0.0221(5) Uani d 1
H H2 0.8029 0.6733 0.8459 0.027 Uiso calc 1
C C3 0.85798(15) 0.4833(2) 0.85452(19) 0.0209(5) Uani d 1
C C4 0.87445(15) 0.3687(2) 0.7877(2) 0.0215(5) Uani d 1
C C5 0.84866(15) 0.3707(2) 0.6697(2) 0.0216(5) Uani d 1
H H5 0.8614 0.2940 0.6248 0.026 Uiso calc 1
C C6 0.80366(15) 0.4851(2) 0.61475(19) 0.0199(5) Uani d 1
C C7 0.77319(15) 0.4805(2) 0.4900(2) 0.0213(5) Uani d 1
H H7 0.7956 0.4063 0.4488 0.026 Uiso calc 1
C C8 0.71704(16) 0.5704(2) 0.4282(2) 0.0218(5) Uani d 1
H H8 0.6945 0.6454 0.4682 0.026 Uiso calc 1
C C9 0.68771(16) 0.5613(2) 0.3027(2) 0.0203(5) Uani d 1
C C10 0.88237(17) 0.5938(2) 1.0373(2) 0.0272(6) Uani d 1
H H10A 0.9172 0.6663 1.0029 0.041 Uiso calc 1
H H10B 0.9117 0.5776 1.1169 0.041 Uiso calc 1
H H10C 0.8151 0.6206 1.0378 0.041 Uiso calc 1
C C11 0.94348(18) 0.1483(2) 0.7837(2) 0.0310(6) Uani d 1
H H11A 0.9848 0.1789 0.7267 0.046 Uiso calc 1
H H11B 0.8855 0.1062 0.7436 0.046 Uiso calc 1
H H11C 0.9783 0.0821 0.8357 0.046 Uiso calc 1
O O5 0.53991(11) 0.37633(14) -0.38715(14) 0.0246(4) Uani d 1
N N1 0.64733(12) 0.45071(17) 0.03376(16) 0.0194(4) Uani d 1
N N2 0.53537(15) 0.60408(19) -0.37305(18) 0.0226(5) Uani d 1
H H2A 0.5516(17) 0.675(2) -0.332(2) 0.029(7) Uiso d 1
H H2B 0.5135(16) 0.610(2) -0.452(2) 0.024(6) Uiso d 1
C C12 0.65593(16) 0.3474(2) -0.0384(2) 0.0222(5) Uani d 1
H H12 0.6838 0.2655 -0.0074 0.027 Uiso calc 1
C C13 0.62619(15) 0.3538(2) -0.15608(19) 0.0200(5) Uani d 1
H H13 0.6343 0.2785 -0.2047 0.024 Uiso calc 1
C C14 0.58421(14) 0.4729(2) -0.20158(19) 0.0176(5) Uani d 1
C C15 0.57285(15) 0.5794(2) -0.12662(19) 0.0201(5) Uani d 1
H H15 0.5431 0.6613 -0.1546 0.024 Uiso calc 1
C C16 0.60561(15) 0.5639(2) -0.01080(19) 0.0203(5) Uani d 1
H H16 0.5981 0.6375 0.0399 0.024 Uiso calc 1
C C17 0.55146(15) 0.4807(2) -0.3288(2) 0.0189(5) Uani d 1
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
C9 O1 H1 107.3(17)
C3 O3 C10 116.27(16)
C4 O4 C11 116.57(18)
C2 C1 H1A 119.3
C2 C1 C6 121.4(2)
C6 C1 H1A 119.3
C1 C2 H2 119.9
C3 C2 C1 120.3(2)
C3 C2 H2 119.9
O3 C3 C2 124.7(2)
O3 C3 C4 115.78(19)
C2 C3 C4 119.5(2)
O4 C4 C3 114.8(2)
O4 C4 C5 125.2(2)
C5 C4 C3 119.9(2)
C4 C5 H5 119.6
C4 C5 C6 120.9(2)
C6 C5 H5 119.6
C1 C6 C5 118.1(2)
C1 C6 C7 122.8(2)
C5 C6 C7 119.1(2)
C6 C7 H7 116.7
C8 C7 C6 126.5(2)
C8 C7 H7 116.7
C7 C8 H8 117.7
C7 C8 C9 124.7(2)
C9 C8 H8 117.7
O1 C9 C8 115.27(18)
O2 C9 O1 123.0(2)
O2 C9 C8 121.7(2)
O3 C10 H10A 109.5
O3 C10 H10B 109.5
O3 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O4 C11 H11A 109.5
O4 C11 H11B 109.5
O4 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C12 N1 C16 117.60(19)
H2A N2 H2B 121(2)
C17 N2 H2A 120.7(16)
C17 N2 H2B 117.4(13)
N1 C12 H12 118.4
N1 C12 C13 123.21(19)
C13 C12 H12 118.4
C12 C13 H13 120.7
C12 C13 C14 118.6(2)
C14 C13 H13 120.7
C13 C14 C17 118.97(19)
C15 C14 C13 118.5(2)
C15 C14 C17 122.55(19)
C14 C15 H15 120.6
C16 C15 C14 118.7(2)
C16 C15 H15 120.6
N1 C16 C15 123.4(2)
N1 C16 H16 118.3
C15 C16 H16 118.3
O5 C17 N2 123.2(2)
O5 C17 C14 120.34(19)
N2 C17 C14 116.50(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1 1.0000(10)
O1 C9 1.322(3)
O2 C9 1.225(2)
O3 C3 1.369(3)
O3 C10 1.434(2)
O4 C4 1.375(2)
O4 C11 1.429(3)
C1 H1A 0.9500
C1 C2 1.382(3)
C1 C6 1.393(3)
C2 H2 0.9500
C2 C3 1.381(3)
C3 C4 1.409(3)
C4 C5 1.378(3)
C5 H5 0.9500
C5 C6 1.410(3)
C6 C7 1.464(3)
C7 H7 0.9500
C7 C8 1.337(3)
C8 H8 0.9500
C8 C9 1.472(3)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
O5 C17 1.234(2)
N1 C12 1.337(3)
N1 C16 1.337(3)
N2 H2A 0.87(2)
N2 H2B 0.93(2)
N2 C17 1.332(3)
C12 H12 0.9500
C12 C13 1.384(3)
C13 H13 0.9500
C13 C14 1.391(3)
C14 C15 1.388(3)
C14 C17 1.499(3)
C15 H15 0.9500
C15 C16 1.379(3)
C16 H16 0.9500
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
O1 H1 N1 . 1.0000(10) 1.609(3) 2.607(2) 176(3)
N2 H2B O5 3_664 0.93(2) 1.94(3) 2.869(3) 176(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O3 C3 C4 O4 0.2(3)
O3 C3 C4 C5 -179.4(2)
O4 C4 C5 C6 178.9(2)
C1 C2 C3 O3 -179.4(2)
C1 C2 C3 C4 -0.1(3)
C1 C6 C7 C8 -8.7(4)
C2 C1 C6 C5 0.5(3)
C2 C1 C6 C7 178.1(2)
C2 C3 C4 O4 -179.13(19)
C2 C3 C4 C5 1.3(3)
C3 C4 C5 C6 -1.5(3)
C4 C5 C6 C1 0.7(3)
C4 C5 C6 C7 -177.0(2)
C5 C6 C7 C8 168.9(2)
C6 C1 C2 C3 -0.8(3)
C6 C7 C8 C9 -179.6(2)
C7 C8 C9 O1 9.3(3)
C7 C8 C9 O2 -171.7(2)
C10 O3 C3 C2 -8.8(3)
C10 O3 C3 C4 171.92(19)
C11 O4 C4 C3 -174.17(19)
C11 O4 C4 C5 5.4(3)
N1 C12 C13 C14 -0.8(3)
C12 N1 C16 C15 -1.0(3)
C12 C13 C14 C15 -0.9(3)
C12 C13 C14 C17 -179.78(19)
C13 C14 C15 C16 1.5(3)
C13 C14 C17 O5 17.5(3)
C13 C14 C17 N2 -163.1(2)
C14 C15 C16 N1 -0.6(3)
C15 C14 C17 O5 -161.4(2)
C15 C14 C17 N2 18.0(3)
C16 N1 C12 C13 1.7(3)
C17 C14 C15 C16 -179.6(2)
