#------------------------------------------------------------------------------
#$Date: 2019-11-28 15:01:03 +0100 (jue 28 de nov de 2019) $
#$Revision: 244078 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/81/7238140.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_7238140
loop_
_publ_author_name
'Omondi, B.'
'Fernandes, M. A.'
'Layh, M.'
'Levendis, D. C.'
'Look, J. L.'
'Mkwizu, T. S. P.'
_publ_section_title
;
 Polymorphism and phase transformations in 2,6-disubstituted
 N-phenylformamides: the influence of hydrogen bonding, chloro-methyl
 exchange, intermolecular interactions and disorder
;
_journal_issue                   114
_journal_name_full               CrystEngComm
_journal_page_first              690
_journal_paper_doi               10.1039/b513882e
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C8 H8 Cl N O'
_chemical_formula_sum            'C8 H8 Cl N O'
_chemical_formula_weight         169.60
_chemical_name_common            2,6-chloromethyl-N-phenylformamide
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4446(2)
_cell_length_b                   12.9028(3)
_cell_length_c                   14.4186(3)
_cell_measurement_reflns_used    5143
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.83
_cell_volume                     1571.04(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11245
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.9205
_exptl_absorpt_correction_T_min  0.8666
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1894
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0505P)²+1.0680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                1696
_reflns_number_total             1894
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b513882e.txt
_cod_data_source_block           5b_bo5_s
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               7238140
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.05300(16) 0.58009(11) 0.14937(9) 0.0198(3) Uani 1 1 d . A .
C2 C 0.14015(17) 0.48978(12) 0.16421(10) 0.0238(3) Uani 1 1 d D . .
C3 C 0.24340(19) 0.45409(13) 0.09646(11) 0.0311(4) Uani 1 1 d . A .
H3 H 0.3047 0.3936 0.1074 0.037 Uiso 1 1 calc R . .
C4 C 0.25738(19) 0.50624(14) 0.01313(11) 0.0336(4) Uani 1 1 d . . .
H4 H 0.3280 0.4814 -0.0331 0.040 Uiso 1 1 calc R A .
C5 C 0.16877(18) 0.59460(13) -0.00323(10) 0.0292(3) Uani 1 1 d . A .
H5 H 0.1772 0.6295 -0.0611 0.035 Uiso 1 1 calc R . .
C6 C 0.06754(16) 0.63239(11) 0.06480(10) 0.0224(3) Uani 1 1 d D . .
C7 C -0.01267(17) 0.65401(12) 0.30021(10) 0.0253(3) Uani 1 1 d . A .
H7 H -0.0950 0.6784 0.3394 0.030 Uiso 1 1 calc R . .
Cl1 Cl 0.11595(16) 0.41946(11) 0.26651(6) 0.03299(18) Uani 0.573(1) 1 d PD A 1
C8 C -0.0263(6) 0.7275(3) 0.0479(4) 0.03299(18) Uani 0.573(1) 1 d PD A 1
H8A H -0.0021 0.7546 -0.0140 0.049 Uiso 0.573(1) 1 calc PR A 1
H8B H 0.0004 0.7797 0.0947 0.049 Uiso 0.573(1) 1 calc PR A 1
H8C H -0.1394 0.7111 0.0519 0.049 Uiso 0.573(1) 1 calc PR A 1
Cl1A Cl -0.04280(19) 0.74302(10) 0.04337(13) 0.03299(18) Uani 0.427(1) 1 d PD A
2
C8A C 0.1286(11) 0.4242(6) 0.2497(4) 0.03299(18) Uani 0.427(1) 1 d PD A 2
H8D H 0.1989 0.3642 0.2435 0.049 Uiso 0.427(1) 1 calc PR A 2
H8E H 0.0193 0.4005 0.2575 0.049 Uiso 0.427(1) 1 calc PR A 2
H8F H 0.1603 0.4652 0.3038 0.049 Uiso 0.427(1) 1 calc PR A 2
N1 N -0.05550(14) 0.61747(10) 0.21718(8) 0.0221(3) Uani 1 1 d . . .
H1 H -0.150(2) 0.6226(15) 0.2026(13) 0.029(5) Uiso 1 1 d . . .
O1 O 0.12208(13) 0.65903(10) 0.33058(8) 0.0341(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0150(6) 0.0253(7) 0.0193(6) -0.0028(5) -0.0010(5) -0.0023(5)
C2 0.0210(6) 0.0269(7) 0.0236(7) -0.0021(5) -0.0043(5) -0.0006(5)
C3 0.0238(7) 0.0346(8) 0.0351(8) -0.0123(7) -0.0046(6) 0.0058(6)
C4 0.0243(7) 0.0480(10) 0.0286(8) -0.0162(7) 0.0043(6) -0.0010(7)
C5 0.0259(7) 0.0412(9) 0.0204(7) -0.0060(6) 0.0026(6) -0.0091(7)
C6 0.0197(6) 0.0260(7) 0.0215(6) -0.0015(5) -0.0021(5) -0.0057(5)
C7 0.0208(7) 0.0331(8) 0.0220(7) -0.0008(6) 0.0034(5) 0.0051(6)
Cl1 0.0384(4) 0.0308(3) 0.0298(3) 0.0073(3) -0.0020(3) 0.0031(2)
C8 0.0384(4) 0.0308(3) 0.0298(3) 0.0073(3) -0.0020(3) 0.0031(2)
Cl1A 0.0384(4) 0.0308(3) 0.0298(3) 0.0073(3) -0.0020(3) 0.0031(2)
C8A 0.0384(4) 0.0308(3) 0.0298(3) 0.0073(3) -0.0020(3) 0.0031(2)
N1 0.0136(5) 0.0311(7) 0.0215(6) 0.0008(5) 0.0007(4) 0.0025(5)
O1 0.0221(5) 0.0531(8) 0.0272(6) -0.0111(5) -0.0035(4) 0.0061(5)
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'
Cl Cl 0.1484 0.1585 '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 119.37(13)
C2 C1 N1 121.14(12)
C6 C1 N1 119.44(13)
C3 C2 C1 120.04(14)
C3 C2 C8A 115.6(4)
C1 C2 C8A 124.3(4)
C3 C2 Cl1 119.76(13)
C1 C2 Cl1 120.18(12)
C4 C3 C2 120.27(15)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 120.20(14)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.09(15)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 120.00(14)
C5 C6 C8 120.3(3)
C1 C6 C8 119.7(3)
C5 C6 Cl1A 119.61(13)
C1 C6 Cl1A 120.38(13)
O1 C7 N1 126.31(14)
O1 C7 H7 116.8
N1 C7 H7 116.8
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C2 C8A H8D 109.5
C2 C8A H8E 109.5
H8D C8A H8E 109.5
C2 C8A H8F 109.5
H8D C8A H8F 109.5
H8E C8A H8F 109.5
C7 N1 C1 124.08(12)
C7 N1 H1 117.3(13)
C1 N1 H1 118.3(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.395(2)
C1 C6 1.3990(19)
C1 N1 1.4241(17)
C2 C3 1.388(2)
C2 C8A 1.497(4)
C2 Cl1 1.7437(17)
C3 C4 1.382(2)
C3 H3 0.9500
C4 C5 1.384(3)
C4 H4 0.9500
C5 C6 1.390(2)
C5 H5 0.9500
C6 C8 1.481(4)
C6 Cl1A 1.7324(18)
C7 O1 1.2210(18)
C7 N1 1.3366(19)
C7 H7 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C8A H8D 0.9800
C8A H8E 0.9800
C8A H8F 0.9800
N1 H1 0.83(2)
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 H1 O1 0.83(2) 2.04(2) 2.8592(17) 171.2(18) 6_556
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
C6 C1 C2 C3 1.8(2)
N1 C1 C2 C3 179.03(13)
C6 C1 C2 C8A -176.8(4)
N1 C1 C2 C8A 0.5(4)
C6 C1 C2 Cl1 -176.52(11)
N1 C1 C2 Cl1 0.75(19)
C1 C2 C3 C4 -1.7(2)
C8A C2 C3 C4 177.0(4)
Cl1 C2 C3 C4 176.62(13)
C2 C3 C4 C5 0.2(2)
C3 C4 C5 C6 1.2(2)
C4 C5 C6 C1 -1.1(2)
C4 C5 C6 C8 179.4(3)
C4 C5 C6 Cl1A -179.95(13)
C2 C1 C6 C5 -0.4(2)
N1 C1 C6 C5 -177.69(13)
C2 C1 C6 C8 179.1(3)
N1 C1 C6 C8 1.8(3)
C2 C1 C6 Cl1A 178.45(12)
N1 C1 C6 Cl1A 1.13(19)
O1 C7 N1 C1 -1.4(3)
C2 C1 N1 C7 67.2(2)
C6 C1 N1 C7 -115.57(16)
