Structure of 2-chloro-N-(p-tolyl)propanamide
Jones, Roderick C.; Twamley, Brendan; Acta Crystallographica, Section E: Crystallographic Communications 74 (2018) 1584–1588; doi:10.1107/s2056989018013889

data_2022634
_publ_section_title
;
 Structure of 2-chloro-N-(p-tolyl)propanamide
;
_journal_coden_ASTM              ACSECI
_journal_coeditor_code           DS2252
_journal_issue                   11
_journal_name_full
;
 Acta Crystallographica, Section E: Crystallographic Communications
;
_journal_page_first              1584
_journal_page_last               1588
_journal_paper_doi               10.1107/s2056989018013889
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'C10 H12 Cl N O'
_chemical_formula_sum            'C10 H12 Cl N O'
_chemical_formula_weight         197.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5053(6)
_cell_length_b                   9.6793(5)
_cell_length_c                   21.8380(13)
_cell_measurement_reflns_used    6677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.84
_cell_volume                     2009.2(2)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type            'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest ECO'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON 50'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19741
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.467
_diffrn_reflns_theta_min         3.536
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0371
_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/[\s^2^(Fo^2^)+(0.0322P)^2^+1.4949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1668
_reflns_number_total             2061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ds2252sup1_1b.cif
_cod_data_source_block           1b
_cod_database_code               2022634
_publcif_datablock.id            {aca8bb5f-3694-4817-9520-5a8102d25299}
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.914
_exptl_absorpt_special_details
;
SADABS (Bruker, 2016a) was used for absorption correction. wR2(int) was 0.0755
 before and 0.0598 after correction. The Ratio of minimum to maximum
 transmission is 0.9411. The \l/2 correction factor is 0.00150.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11-C12A = C12-C11
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C12A) = Uanis(C12)
4. Others
 Sof(Cl1A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=1-FVAR(1)
 Sof(Cl1)=Sof(H11)=Sof(C12)=Sof(H12D)=Sof(H12E)=Sof(H12F)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C11(H11A)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C12A(H12A,H12B,H12C), C12(H12D,H12E,H12F)
;
_iucr_geom_hbonds_special_details
;
Cg1 is the centroid of the C1--C6 ring.
;
_shelx_res_checksum              81333
_shelx_hkl_checksum              90578
_olex2_exptl_crystal_mounting_method 'mounted in oil on a Mitegen holder'
_olex2_submission_original_sample_id RCJ1-3
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;<span class="funder"><span class="fundref-name" data-id="">Synthesis and Solid 
State Pharmaceutical Center (SSPC)</span><span class="fundref-subname" 
data-id=""></span><span class="fundref-grant"></span>; </span><span 
class="funder"><span class="fundref-name" data-id="">Science Foundation
Ireland</span><span class="fundref-subname" data-id=""></span> (<span 
class="fundref-grant-group"><span class="fundref-grant-type">grant</span> No. 
<span class="fundref-grant-id">SFI, 12/RC/2275</span></span>).</span>
;
_cod_database_fobs_code 2022634