#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:10:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179655 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/08/4510803.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_4510803
loop_
_publ_author_name
'Zipp, Caitlin F.'
'Dirr, Heini W.'
'Fernandes, Manuel A.'
'Marques, Helder M.'
'Michael, Joseph P.'
_publ_section_title
;
 Polymorphic Diversity:N-Phenylbenzamide as a Possible Polymorphophore
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3463
_journal_paper_doi               10.1021/cg400356s
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C21 H17 N O3'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.091(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9682(3)
_cell_length_b                   12.0166(6)
_cell_length_c                   22.9633(12)
_cell_measurement_reflns_used    4280
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.32
_cell_measurement_theta_min      3.85
_cell_volume                     1646.87(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1445
_diffrn_reflns_av_sigmaI/netI    0.0997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7748
_diffrn_reflns_theta_full        62.48
_diffrn_reflns_theta_max         62.48
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0710P)²+2.2894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                2277
_reflns_number_total             2512
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c10_czhmmp7_0f-cmpd5a.cif
_cod_data_source_block           c10_czhmmp7_0f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4510803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.6465(7) 0.6621(3) 0.83692(16) 0.0218(9) Uani 1 1 d .
H1A H 0.4952 0.6450 0.8216 0.026 Uiso 1 1 calc R
H1B H 0.7504 0.6662 0.8034 0.026 Uiso 1 1 calc R
C2 C 0.6408(7) 0.7737(3) 0.86698(16) 0.0224(9) Uani 1 1 d .
C3 C 0.4582(8) 0.7967(4) 0.90364(17) 0.0291(10) Uani 1 1 d .
H3 H 0.3492 0.7407 0.9106 0.035 Uiso 1 1 calc R
C4 C 0.4351(9) 0.9002(4) 0.92983(18) 0.0337(10) Uani 1 1 d .
H4 H 0.3088 0.9155 0.9537 0.040 Uiso 1 1 calc R
C5 C 0.5952(9) 0.9805(4) 0.92119(18) 0.0367(12) Uani 1 1 d .
H5 H 0.5790 1.0510 0.9394 0.044 Uiso 1 1 calc R
C6 C 0.7806(9) 0.9603(4) 0.88628(18) 0.0317(11) Uani 1 1 d .
H6 H 0.8920 1.0160 0.8814 0.038 Uiso 1 1 calc R
C7 C 0.8024(7) 0.8564(3) 0.85808(16) 0.0227(9) Uani 1 1 d .
C8 C 1.1031(7) 0.9082(3) 0.78746(17) 0.0267(10) Uani 1 1 d .
C9 C 1.2808(7) 0.8557(3) 0.74959(16) 0.0247(9) Uani 1 1 d .
C10 C 1.4724(8) 0.9172(4) 0.73763(17) 0.0288(10) Uani 1 1 d .
H10 H 1.4870 0.9901 0.7532 0.035 Uiso 1 1 calc R
C11 C 1.6424(8) 0.8742(4) 0.70339(18) 0.0379(12) Uani 1 1 d .
H11 H 1.7729 0.9170 0.6958 0.046 Uiso 1 1 calc R
C12 C 1.6209(8) 0.7685(4) 0.68031(19) 0.0361(12) Uani 1 1 d .
H12 H 1.7372 0.7384 0.6569 0.043 Uiso 1 1 calc R
C13 C 1.4287(9) 0.7060(4) 0.69133(18) 0.0336(11) Uani 1 1 d .
H13 H 1.4129 0.6339 0.6749 0.040 Uiso 1 1 calc R
C14 C 1.2598(8) 0.7494(4) 0.72642(17) 0.0288(10) Uani 1 1 d .
H14 H 1.1302 0.7062 0.7345 0.035 Uiso 1 1 calc R
C15 C 0.9356(7) 0.5557(3) 0.88052(16) 0.0200(8) Uani 1 1 d .
C16 C 0.9855(7) 0.4567(3) 0.91704(15) 0.0188(9) Uani 1 1 d .
C17 C 0.8317(8) 0.3722(4) 0.92521(18) 0.0282(10) Uani 1 1 d .
H17 H 0.6882 0.3766 0.9074 0.034 Uiso 1 1 calc R
C18 C 0.8867(9) 0.2811(4) 0.9593(2) 0.0367(11) Uani 1 1 d .
H18 H 0.7818 0.2225 0.9643 0.044 Uiso 1 1 calc R
C19 C 1.0930(9) 0.2755(4) 0.98580(19) 0.0356(11) Uani 1 1 d .
H19 H 1.1290 0.2140 1.0100 0.043 Uiso 1 1 calc R
C20 C 1.2461(8) 0.3582(4) 0.97740(17) 0.0294(10) Uani 1 1 d .
H20 H 1.3883 0.3533 0.9958 0.035 Uiso 1 1 calc R
C21 C 1.1982(8) 0.4494(3) 0.94247(17) 0.0247(9) Uani 1 1 d .
H21 H 1.3073 0.5056 0.9360 0.030 Uiso 1 1 calc R
N1 N 0.9870(6) 0.8348(3) 0.82073(15) 0.0266(8) Uani 1 1 d .
H1 H 1.0317 0.7651 0.8189 0.032 Uiso 1 1 calc R
O1 O 0.7168(5) 0.5728(2) 0.87507(11) 0.0229(6) Uani 1 1 d .
O2 O 1.0695(6) 1.0083(2) 0.78693(14) 0.0387(8) Uani 1 1 d .
O3 O 1.0777(5) 0.6137(2) 0.85827(13) 0.0282(7) Uani 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 0.0181 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 112.9(3)
O1 C1 H1A 109.0
C2 C1 H1A 109.0
O1 C1 H1B 109.0
C2 C1 H1B 109.0
H1A C1 H1B 107.8
C7 C2 C3 118.9(4)
C7 C2 C1 123.3(4)
C3 C2 C1 117.8(4)
C4 C3 C2 120.9(4)
C4 C3 H3 119.6
C2 C3 H3 119.6
C5 C4 C3 119.8(4)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 121.1(4)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C7 119.5(4)
C5 C6 H6 120.2
C7 C6 H6 120.2
C2 C7 C6 119.8(4)
C2 C7 N1 119.6(3)
C6 C7 N1 120.7(4)
O2 C8 N1 124.2(4)
O2 C8 C9 121.4(4)
N1 C8 C9 114.4(4)
C14 C9 C10 119.2(4)
C14 C9 C8 122.8(4)
C10 C9 C8 118.0(4)
C11 C10 C9 121.1(4)
C11 C10 H10 119.4
C9 C10 H10 119.4
C12 C11 C10 119.6(5)
C12 C11 H11 120.2
C10 C11 H11 120.2
C11 C12 C13 120.0(5)
C11 C12 H12 120.0
C13 C12 H12 120.0
C14 C13 C12 120.0(4)
C14 C13 H13 120.0
C12 C13 H13 120.0
C9 C14 C13 120.1(4)
C9 C14 H14 120.0
C13 C14 H14 120.0
O3 C15 O1 124.1(4)
O3 C15 C16 124.0(4)
O1 C15 C16 111.9(3)
C17 C16 C21 120.0(4)
C17 C16 C15 122.2(4)
C21 C16 C15 117.8(3)
C16 C17 C18 120.0(4)
C16 C17 H17 120.0
C18 C17 H17 120.0
C19 C18 C17 120.1(4)
C19 C18 H18 120.0
C17 C18 H18 120.0
C20 C19 C18 120.1(4)
C20 C19 H19 120.0
C18 C19 H19 120.0
C19 C20 C21 121.3(4)
C19 C20 H20 119.3
C21 C20 H20 119.3
C20 C21 C16 118.5(4)
C20 C21 H21 120.8
C16 C21 H21 120.8
C8 N1 C7 128.2(4)
C8 N1 H1 115.9
C7 N1 H1 115.9
C15 O1 C1 117.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.447(5)
C1 C2 1.509(6)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C7 1.400(6)
C2 C3 1.406(6)
C3 C4 1.389(6)
C3 H3 0.9500
C4 C5 1.372(7)
C4 H4 0.9500
C5 C6 1.388(7)
C5 H5 0.9500
C6 C7 1.413(6)
C6 H6 0.9500
C7 N1 1.421(6)
C8 O2 1.220(5)
C8 N1 1.357(5)
C8 C9 1.510(6)
C9 C14 1.389(6)
C9 C10 1.390(6)
C10 C11 1.385(7)
C10 H10 0.9500
C11 C12 1.382(7)
C11 H11 0.9500
C12 C13 1.394(7)
C12 H12 0.9500
C13 C14 1.392(7)
C13 H13 0.9500
C14 H14 0.9500
C15 O3 1.211(5)
C15 O1 1.327(5)
C15 C16 1.486(5)
C16 C17 1.382(6)
C16 C21 1.399(6)
C17 C18 1.384(6)
C17 H17 0.9500
C18 C19 1.375(7)
C18 H18 0.9500
C19 C20 1.364(7)
C19 H19 0.9500
C20 C21 1.387(6)
C20 H20 0.9500
C21 H21 0.9500
N1 H1 0.8800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O3 0.88 2.05 2.845(4) 150
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
O1 C1 C2 C7 105.2(4)
O1 C1 C2 C3 -77.7(4)
C7 C2 C3 C4 1.2(6)
C1 C2 C3 C4 -176.0(4)
C2 C3 C4 C5 -1.7(6)
C3 C4 C5 C6 0.4(7)
C4 C5 C6 C7 1.5(6)
C3 C2 C7 C6 0.6(6)
C1 C2 C7 C6 177.7(4)
C3 C2 C7 N1 -179.4(3)
C1 C2 C7 N1 -2.4(5)
C5 C6 C7 C2 -1.9(6)
C5 C6 C7 N1 178.1(4)
O2 C8 C9 C14 -147.6(4)
N1 C8 C9 C14 31.8(5)
O2 C8 C9 C10 32.2(6)
N1 C8 C9 C10 -148.3(4)
C14 C9 C10 C11 -0.3(6)
C8 C9 C10 C11 179.8(4)
C9 C10 C11 C12 0.5(6)
C10 C11 C12 C13 0.3(6)
C11 C12 C13 C14 -1.1(6)
C10 C9 C14 C13 -0.5(6)
C8 C9 C14 C13 179.4(3)
C12 C13 C14 C9 1.2(6)
O3 C15 C16 C17 -157.4(4)
O1 C15 C16 C17 22.4(5)
O3 C15 C16 C21 21.1(5)
O1 C15 C16 C21 -159.1(3)
C21 C16 C17 C18 1.0(6)
C15 C16 C17 C18 179.5(4)
C16 C17 C18 C19 1.1(7)
C17 C18 C19 C20 -1.7(7)
C18 C19 C20 C21 0.3(7)
C19 C20 C21 C16 1.8(6)
C17 C16 C21 C20 -2.4(6)
C15 C16 C21 C20 179.0(4)
O2 C8 N1 C7 3.5(7)
C9 C8 N1 C7 -176.0(4)
C2 C7 N1 C8 149.7(4)
C6 C7 N1 C8 -30.3(6)
O3 C15 O1 C1 4.2(5)
C16 C15 O1 C1 -175.6(3)
C2 C1 O1 C15 -85.8(4)
