Preferential N–H⋯:C hydrogen bonding involving ditopic NH-containing systems and N-heterocyclic carbenes
Kinney, Zacharias J.; Rheingold, Arnold L.; Protasiewicz, John D.; RSC Advances 10 (2020) 42164–42171; doi:10.1039/D0RA08490E

data_7241627
_publ_section_title
;
 Preferential N--H&#x22EF;:C&#xE00A; hydrogen bonding involving ditopic
 NH-containing systems and N-heterocyclic carbenes
;
_journal_issue                   69
_journal_name_full               'RSC Advances'
_journal_page_first              42164
_journal_page_last               42171
_journal_paper_doi               10.1039/D0RA08490E
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 N2'
_chemical_formula_sum            'C24 H18 N2'
_chemical_formula_weight         334.40
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-22 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                98.0950(10)
_cell_angle_beta                 90.7670(10)
_cell_angle_gamma                90.0300(10)
_cell_formula_units_Z            4
_cell_length_a                   9.7054(2)
_cell_length_b                   9.9914(2)
_cell_length_c                   17.4974(3)
_cell_measurement_reflns_used    9803
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      2.55
_cell_volume                     1679.67(6)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            46621
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.389
_diffrn_reflns_theta_min         2.551
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0650 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.8850.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 4757 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     937
_refine_ls_number_reflns         11741
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0780P)^2^+0.1836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                10562
_reflns_number_total             11741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra08490e2.cif
_cod_data_source_block           pro172_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7241627
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.827
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N2A(H2AA), N2B(H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N2C(H2C), N1A(H1A), N1C(H1C), N1B(H1B), N1(H1), C8A(H8A), C10C(H10C),
 C10(H10), C10B(H10B), C24(H24), C11B(H11B), C24B(H24B), C24C(H24C), C17A(H17A),
  C8B(H8B), C8C(H8C), C24A(H24A), C10A(H10A), C5A(H5A), C8(H8), C11A(H11A),
 C11(H11), C2C(H2CA), C5(H5), C17B(H17B), C11C(H11C), C2(H2A), C20B(H20B),
 C5C(H5C), C5B(H5B), C3B(H3B), C20(H20), C20A(H20A), C14(H14), C17C(H17C),
 C2B(H2BA), C23A(H23A), C23B(H23B), C17(H17), C15C(H15C), C23(H23), C18C(H18C),
 C14C(H14C), C3C(H3C), C3A(H3A), C3(H3), C23C(H23C), C20C(H20C), C15(H15),
 C4A(H4A), C2A(H2AB), C21A(H21A), C4B(H4B), C4(H4), C18A(H18A), C18B(H18B),
 C4C(H4C), C21C(H21C), C21(H21), C15A(H15A), C14B(H14B), C22(H22), C21B(H21B),
 C14A(H14A), C15B(H15B), C22C(H22C), C22B(H22B), C18(H18), C22A(H22A)
;
_shelx_res_checksum              8835
_olex2_submission_special_instructions 'No special instructions were received'