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_7241625
_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_formula_moiety         '2(C27 H36 N2), 2(C12 H8 N), C4 H8 O'
_chemical_formula_sum            'C82 H96 N6 O'
_chemical_formula_weight         1181.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2019-05-23
_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                78.6270(10)
_cell_angle_beta                 72.4790(10)
_cell_angle_gamma                74.7170(10)
_cell_formula_units_Z            2
_cell_length_a                   13.7938(2)
_cell_length_b                   14.3012(2)
_cell_length_c                   19.4614(2)
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.285
_cell_measurement_theta_min      3.230
_cell_volume                     3502.43(8)
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            56480
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.344
_diffrn_reflns_theta_min         2.400
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0715 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.8964. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       block
_exptl_crystal_F_000             1276
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     822
_refine_ls_number_reflns         12561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+1.6544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11159
_reflns_number_total             12561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra08490e2.cif
_cod_data_source_block           cwru01_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_original_cell_volume        3502.44(8)
_cod_database_code               7241625
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.868
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C37(H37), C22(H22), C22'(H22'), C34(H34), C34'(H34'), C25(H25), C25'(H25'),
 C37'(H37')
2.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C41(H41A,H41B), C43(H43A,H43B), C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 N1'(H1'), C5(H5), C5'(H5'), C15(H15), C3'(H3'), C14(H14), C11(H11), C3(H3),
 C14'(H14'), C32(H32), C18(H18), C8(H8), C15'(H15'), C2'(H2'), C8'(H8'), C2(H2),
  C11'(H11'), C9'(H9'), C19(H19), C30(H30), C10'(H10'), C31(H31), C30'(H30'),
 C10(H10), C9(H9), C18'(H18'), C20(H20), C20'(H20'), C19'(H19'), C31'(H31'),
 C32'(H32')
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C38(H38A,H38B,H38C), C23'(H23D,H23E,H23F), C24(H24A,H24B,
 H24C), C24'(H24D,H24E,H24F), C35'(H35D,H35E,H35F), C36'(H36D,H36E,H36F),
 C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C39'(H39D,H39E,
 H39F), C35(H35A,H35B,H35C), C38'(H38D,H38E,H38F), C36(H36A,H36B,H36C),
 C26'(H26D,H26E,H26F), C27'(H27D,H27E,H27F)
;
_shelx_res_checksum              51599
_olex2_submission_special_instructions 'No special instructions were received'