#------------------------------------------------------------------------------
#$Date: 2019-11-28 16:01:03 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/81/7238141.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_7238141
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           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 111.365(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.498(3)
_cell_length_b                   4.3186(10)
_cell_length_c                   14.938(3)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.144
_cell_measurement_theta_min      3.242
_cell_volume                     810.9(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9940
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.9681
_exptl_absorpt_correction_T_min  0.7919
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1951
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0504P)²+0.3441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1111
_reflns_number_gt                1619
_reflns_number_total             1951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b513882e.txt
_cod_data_source_block           26clmeht
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'None' was changed
to 'none' 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.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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      P2(1)/a
_cod_database_code               7238141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'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 0.21614(11) 0.5970(3) 0.26193(10) 0.0293(3) Uani 1 1 d U A .
C2 C 0.13667(11) 0.4688(4) 0.28999(11) 0.0337(3) Uani 1 1 d U . .
C3 C 0.05369(13) 0.3058(4) 0.22300(13) 0.0450(4) Uani 1 1 d U A .
H3 H -0.0003 0.2180 0.2417 0.054 Uiso 1 1 calc R . .
C4 C 0.04883(14) 0.2700(5) 0.12995(13) 0.0525(5) Uani 1 1 d U . .
H4 H -0.0082 0.1574 0.0851 0.063 Uiso 1 1 calc R A .
C5 C 0.12640(15) 0.3969(5) 0.10141(12) 0.0514(5) Uani 1 1 d U A .
H5 H 0.1227 0.3726 0.0371 0.062 Uiso 1 1 calc R . .
C6 C 0.21004(12) 0.5604(4) 0.16736(11) 0.0376(4) Uani 1 1 d U . .
C7 C 0.38573(12) 0.6113(3) 0.39388(11) 0.0348(3) Uani 1 1 d U A .
H7 H 0.4409 0.7338 0.4372 0.042 Uiso 1 1 calc R . .
Cl1 Cl 0.31038(13) 0.7287(4) 0.13461(12) 0.0587(4) Uani 0.750(2) 1 d PU A 1
C8 C 0.1382(11) 0.498(3) 0.3911(7) 0.058(2) Uani 0.750(2) 1 d PU A 1
H8A H 0.0770 0.3879 0.3963 0.087 Uiso 0.750(2) 1 calc PR A 1
H8B H 0.1346 0.7171 0.4066 0.087 Uiso 0.750(2) 1 calc PR A 1
H8C H 0.2041 0.4075 0.4362 0.087 Uiso 0.750(2) 1 calc PR A 1
Cl1A Cl 0.1446(8) 0.551(2) 0.4067(6) 0.0535(12) Uani 0.250(2) 1 d PU A 2
C8A C 0.2951(16) 0.691(5) 0.1341(11) 0.061(5) Uani 0.250(2) 1 d PU A 2
H8D H 0.2773 0.6430 0.0659 0.092 Uiso 0.250(2) 1 calc PR A 2
H8E H 0.3640 0.5984 0.1718 0.092 Uiso 0.250(2) 1 calc PR A 2
H8F H 0.2990 0.9161 0.1431 0.092 Uiso 0.250(2) 1 calc PR A 2
N1 N 0.30304(10) 0.7585(3) 0.33011(9) 0.0317(3) Uani 1 1 d U . .
O1 O 0.39537(10) 0.3295(3) 0.40036(10) 0.0559(4) Uani 1 1 d U . .
H1 H 0.3064(16) 0.950(5) 0.3325(14) 0.050(5) Uiso 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 0.0282(6) 0.0233(6) 0.0339(7) 0.0014(5) 0.0082(5) 0.0051(5)
C2 0.0305(7) 0.0330(7) 0.0354(7) 0.0030(6) 0.0092(6) 0.0035(6)
C3 0.0301(8) 0.0416(9) 0.0548(10) 0.0027(7) 0.0053(7) -0.0019(6)
C4 0.0390(9) 0.0505(11) 0.0512(10) -0.0107(8) -0.0036(8) 0.0023(8)
C5 0.0497(10) 0.0621(12) 0.0333(8) -0.0086(8) 0.0043(7) 0.0156(9)
C6 0.0361(8) 0.0405(8) 0.0371(8) 0.0042(6) 0.0142(6) 0.0114(6)
C7 0.0286(7) 0.0262(7) 0.0442(8) -0.0041(6) 0.0068(6) -0.0021(5)
Cl1 0.0560(6) 0.0748(7) 0.0577(7) 0.0184(5) 0.0356(5) 0.0136(5)
C8 0.045(3) 0.072(5) 0.058(4) 0.004(3) 0.020(3) -0.011(2)
Cl1A 0.046(2) 0.076(3) 0.0441(16) 0.0007(18) 0.0227(15) -0.0081(17)
C8A 0.071(9) 0.092(11) 0.021(5) -0.023(6) 0.017(5) -0.017(7)
N1 0.0320(6) 0.0202(6) 0.0405(7) -0.0014(5) 0.0104(5) -0.0001(5)
O1 0.0407(7) 0.0252(6) 0.0753(9) -0.0017(6) -0.0103(6) 0.0013(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
C6 C1 C2 119.33(13)
C6 C1 N1 120.62(13)
C2 C1 N1 120.04(13)
C3 C2 C1 119.25(15)
C3 C2 C8 118.4(5)
C1 C2 C8 122.3(5)
C3 C2 Cl1A 124.2(3)
C1 C2 Cl1A 116.4(3)
C4 C3 C2 120.87(16)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 120.35(16)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 119.64(16)
C4 C5 H5 120.2
C6 C5 H5 120.2
C5 C6 C1 120.57(16)
C5 C6 C8A 118.2(6)
C1 C6 C8A 121.2(6)
C5 C6 Cl1 121.49(14)
C1 C6 Cl1 117.94(13)
O1 C7 N1 124.54(14)
O1 C7 H7 117.7
N1 C7 H7 117.7
C2 C8 H8A 109.5
C2 C8 H8B 109.5
H8A C8 H8B 109.5
C2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C6 C8A H8D 109.5
C6 C8A H8E 109.5
H8D C8A H8E 109.5
C6 C8A H8F 109.5
H8D C8A H8F 109.5
H8E C8A H8F 109.5
C7 N1 C1 122.24(12)
C7 N1 H1 115.2(14)
C1 N1 H1 122.5(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.394(2)
C1 C2 1.400(2)
C1 N1 1.4245(18)
C2 C3 1.391(2)
C2 C8 1.509(9)
C2 Cl1A 1.744(8)
C3 C4 1.376(3)
C3 H3 0.9500
C4 C5 1.380(3)
C4 H4 0.9500
C5 C6 1.390(3)
C5 H5 0.9500
C6 C8A 1.52(2)
C6 Cl1 1.756(2)
C7 O1 1.224(2)
C7 N1 1.335(2)
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) 2.07(2) 2.7896(18) 145.7(19) 1_565
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 0.4(2)
N1 C1 C2 C3 -178.55(13)
C6 C1 C2 C8 179.7(7)
N1 C1 C2 C8 0.8(7)
C6 C1 C2 Cl1A -175.1(4)
N1 C1 C2 Cl1A 5.9(4)
C1 C2 C3 C4 -0.1(2)
C8 C2 C3 C4 -179.5(7)
Cl1A C2 C3 C4 175.0(5)
C2 C3 C4 C5 -0.2(3)
C3 C4 C5 C6 0.3(3)
C4 C5 C6 C1 0.0(3)
C4 C5 C6 C8A 178.8(11)
C4 C5 C6 Cl1 -179.57(15)
C2 C1 C6 C5 -0.4(2)
N1 C1 C6 C5 178.59(14)
C2 C1 C6 C8A -179.1(11)
N1 C1 C6 C8A -0.1(11)
C2 C1 C6 Cl1 179.22(12)
N1 C1 C6 Cl1 -1.8(2)
O1 C7 N1 C1 0.0(3)
C6 C1 N1 C7 -99.71(18)
C2 C1 N1 C7 79.27(18)
