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_7241626
_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), C18 H16 N2'
_chemical_formula_sum            'C72 H88 N6'
_chemical_formula_weight         1037.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-02
_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                90
_cell_angle_beta                 94.3400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2815(2)
_cell_length_b                   10.7523(3)
_cell_length_c                   23.4308(4)
_cell_measurement_reflns_used    6919
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.217
_cell_measurement_theta_min      3.784
_cell_volume                     3085.27(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19666
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.215
_diffrn_reflns_theta_min         3.784
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0562 before and 0.0370 after correction. The Ratio of minimum to maximum transmission is 0.8959. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0629P)^2^+1.3455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4642
_reflns_number_total             5642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra08490e2.cif
_cod_data_source_block           pro156_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               7241626
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.871
_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. Others
 Fixed Sof: H34(0.5) H34A(0.5) C36'(0.5) H36A(0.5) H36B(0.5) H36C(0.5)
 C35'(0.5) H35A(0.5) H35B(0.5) H35C(0.5) C36(0.5) H36D(0.5) H36E(0.5) H36F(0.5)
 C35(0.5) H35D(0.5) H35E(0.5) H35F(0.5)
3.a Ternary CH refined with riding coordinates:
 C10(H10), C31(H31), C34(H34), C34(H34A), C19(H19)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C1(H1A), C9(H9), C14(H14), C16(H16), C27(H27), C28(H28),
 C5(H5), C29(H29), C8(H8), C23(H23), C22(H22), C6(H6), C7(H7)
3.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C12(H12A,H12B,H12C), C33(H33A,H33B,H33C), C11(H11A,H11B,
 H11C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C36'(H36A,H36B,H36C),
 C35'(H35A,H35B,H35C), C36(H36D,H36E,H36F), C35(H35D,H35E,H35F)
;
_shelx_res_checksum              92717
_olex2_submission_special_instructions 'No special instructions were received'