#------------------------------------------------------------------------------
#$Date: 2019-11-24 23:32:14 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/70/4517047.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_4517047
loop_
_publ_author_name
'Back, Kevin R.'
'Davey, Roger J.'
'Grecu, Tudor'
'Hunter, Christopher A.'
'Taylor, Lynne S.'
_publ_section_title
;
 Molecular Conformation and Crystallization: The Case of Ethenzamide
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6110
_journal_paper_doi               10.1021/cg301244x
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C9 H11 N O2'
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_chemical_melting_point          402
_chemical_name_systematic        2-ethoxybenzamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-06
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_audit_update_record
;
2012-07-09 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0339(5)
_cell_length_b                   11.8782(13)
_cell_length_c                   14.1229(15)
_cell_measurement_reflns_used    2261
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.3312
_cell_measurement_theta_min      3.3618
_cell_volume                     838.88(15)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8.3367
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -56.00   35.00   1.0000   58.6200
omega____ theta____ kappa____ phi______ frames
    -      -21.6996   77.0000 -120.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega  -58.00   71.00   1.0000   58.6200
omega____ theta____ kappa____ phi______ frames
    -      -21.6996   77.0000  -30.0000 129

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00  109.00   1.0000   58.6200
omega____ theta____ kappa____ phi______ frames
    -       23.1058   77.0000   90.0000 125

#__ type_ start__ end____ width___ exp.time_
  4 omega   93.00  122.00   1.0000   58.6200
omega____ theta____ kappa____ phi______ frames
    -       23.1058   77.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   44.00   1.0000   58.6200
omega____ theta____ kappa____ phi______ frames
    -       23.1058   77.0000 -180.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0470661746
_diffrn_orient_matrix_UB_12      0.0216783553
_diffrn_orient_matrix_UB_13      0.0177006034
_diffrn_orient_matrix_UB_21      0.0183898540
_diffrn_orient_matrix_UB_22      -0.0557233868
_diffrn_orient_matrix_UB_23      0.0032712044
_diffrn_orient_matrix_UB_31      0.0005898598
_diffrn_orient_matrix_UB_32      0.0013754889
_diffrn_orient_matrix_UB_33      -0.1407668353
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5595
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_preparation       'Aldrich as supplied'
_exptl_crystal_recrystallization_method
'Cooling crystallisation from acetonitrile'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0504
_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)+(0.0722P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                1164
_reflns_number_total             1942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301244x_si_002.cif
_cod_data_source_block           ord76
_cod_database_code               4517047
_chemical_oxdiff_formula         C9N1O2H11
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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 0.2138(3) 0.78065(12) 0.65687(10) 0.0194(4) Uani 1 1 d .
O2 O 0.3142(2) 0.55836(12) 0.59454(10) 0.0189(4) Uani 1 1 d .
C3 C 0.5388(4) 0.59932(16) 0.62159(14) 0.0148(5) Uani 1 1 d .
C5 C 0.8358(4) 0.70015(19) 0.86509(15) 0.0224(5) Uani 1 1 d .
H5 H 0.9794 0.6808 0.9119 0.027 Uiso 1 1 calc R
C6 C 0.4124(4) 0.75655(17) 0.72853(14) 0.0160(5) Uani 1 1 d .
C7 C 0.5816(4) 0.66703(17) 0.71176(14) 0.0145(5) Uani 1 1 d .
C10 C 0.7952(4) 0.64089(18) 0.77979(14) 0.0186(5) Uani 1 1 d .
H10 H 0.9145 0.5820 0.7678 0.022 Uiso 1 1 calc R
C8 C 0.4546(4) 0.81716(18) 0.81384(15) 0.0204(5) Uani 1 1 d .
H8 H 0.3404 0.8780 0.8255 0.025 Uiso 1 1 calc R
C9 C 0.6655(4) 0.78733(19) 0.88116(15) 0.0227(5) Uani 1 1 d .
H9 H 0.6931 0.8277 0.9395 0.027 Uiso 1 1 calc R
C11 C 0.0581(4) 0.88084(17) 0.66552(15) 0.0200(5) Uani 1 1 d .
H11A H 0.1757 0.9478 0.6722 0.024 Uiso 1 1 calc R
H11B H -0.0399 0.8760 0.7223 0.024 Uiso 1 1 calc R
C12 C -0.1354(4) 0.88930(18) 0.57607(16) 0.0233(5) Uani 1 1 d .
H12A H -0.0364 0.8878 0.5203 0.035 Uiso 1 1 calc R
H12B H -0.2358 0.9599 0.5767 0.035 Uiso 1 1 calc R
H12C H -0.2599 0.8256 0.5731 0.035 Uiso 1 1 calc R
N1 N 0.7478(4) 0.58481(16) 0.57473(14) 0.0202(5) Uani 1 1 d .
H1A H 0.733(4) 0.5452(19) 0.5201(17) 0.025(6) Uiso 1 1 d .
H1B H 0.908(5) 0.606(2) 0.5975(18) 0.035(7) 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'
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'
H H 0.0000 0.0000 '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
C6 O1 C11 117.98(15)
O2 C3 C7 120.32(18)
O2 C3 N1 122.83(19)
N1 C3 C7 116.84(17)
C9 C5 C10 119.36(19)
O1 C6 C7 116.16(17)
O1 C6 C8 123.74(18)
C8 C6 C7 120.09(18)
C6 C7 C3 121.32(17)
C10 C7 C3 119.37(18)
C10 C7 C6 119.31(18)
C5 C10 C7 120.7(2)
C9 C8 C6 119.2(2)
C5 C9 C8 121.3(2)
O1 C11 C12 106.87(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.369(2)
O1 C11 1.438(2)
O2 C3 1.250(2)
C3 C7 1.501(3)
C3 N1 1.317(3)
C5 C10 1.390(3)
C5 C9 1.380(3)
C6 C7 1.400(3)
C6 C8 1.399(3)
C7 C10 1.392(3)
C8 C9 1.387(3)
C11 C12 1.508(3)
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
_geom_hbond_site_symmetry_A
N1 H1B O2 0.87(3) 2.13(3) 2.851(2) 140(2) 1_655
