#------------------------------------------------------------------------------
#$Date: 2021-09-07 02:04:56 +0300 (Tue, 07 Sep 2021) $
#$Revision: 268984 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/81/7708198.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_7708198
loop_
_publ_author_name
'Vrána, Jan'
'Němec, Vlastimil'
'Samsonov, Maksim Andreevich'
'R°užička, Aleš'
_publ_section_title
;
 On the edge of the steric repulsion and reactivity of bulky anilines; a
 case study of chloro(imino)phosphine synthesis
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT02445K
_journal_year                    2021
_chemical_formula_sum            'C34 H27 N O'
_chemical_formula_weight         465.56
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2021-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                102.708(11)
_cell_angle_beta                 97.662(12)
_cell_angle_gamma                98.134(11)
_cell_formula_units_Z            2
_cell_length_a                   5.4624(11)
_cell_length_b                   13.410(3)
_cell_length_c                   17.986(4)
_cell_measurement_reflns_used    18008
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1253.7(5)
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1103
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18008
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.190
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.107(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.1089
_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/[σ²(Fo²)+(0.1426P)²+2.8596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2763
_refine_ls_wR_factor_ref         0.2953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3271
_reflns_number_total             4859
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02445k2.cif
_cod_data_source_block           jvr190812n2a
_cod_original_cell_volume        1253.6(5)
_cod_database_code               7708198
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.750
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9726(7) 0.0730(3) 0.1513(2) 0.0423(9) Uani 1 1 d . . . . .
N1 N 0.9898(6) 0.2307(3) 0.2436(2) 0.0266(8) Uani 1 1 d . . . . .
C1 C 0.8300(7) 0.2941(3) 0.2795(2) 0.0234(9) Uani 1 1 d . . . . .
C2 C 0.7530(7) 0.3705(3) 0.2453(2) 0.0226(9) Uani 1 1 d . . . . .
C3 C 0.6014(8) 0.4335(3) 0.2824(3) 0.0258(9) Uani 1 1 d . . . . .
H3 H 0.5462 0.4859 0.2598 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5281(8) 0.4215(3) 0.3520(2) 0.0256(9) Uani 1 1 d . . . . .
C5 C 0.6140(8) 0.3453(3) 0.3849(2) 0.0260(9) Uani 1 1 d . . . . .
H5 H 0.5674 0.3372 0.4325 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8346(8) 0.3814(3) 0.1689(2) 0.0241(9) Uani 1 1 d . . . . .
H7 H 1.0198 0.3824 0.1763 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7663(7) 0.2808(3) 0.3499(2) 0.0224(9) Uani 1 1 d . . . . .
C9 C 0.4920(8) 0.2268(3) 0.1002(3) 0.0267(9) Uani 1 1 d . . . . .
H9 H 0.4039 0.2414 0.1424 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7194(7) 0.2892(3) 0.1020(2) 0.0229(9) Uani 1 1 d . . . . .
C10 C 0.3907(9) 0.1425(4) 0.0371(3) 0.0329(10) Uani 1 1 d . . . . .
H10 H 0.2352 0.1002 0.0364 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5189(9) 0.1213(4) -0.0244(3) 0.0339(11) Uani 1 1 d . . . . .
H11 H 0.4518 0.0639 -0.0672 0.041 Uiso 1 1 calc R U . . .
C12 C 0.7432(9) 0.1833(4) -0.0237(3) 0.0336(11) Uani 1 1 d . . . . .
H12 H 0.8293 0.1691 -0.0663 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8439(8) 0.2662(3) 0.0389(3) 0.0292(10) Uani 1 1 d . . . . .
H13 H 0.9996 0.3080 0.0389 0.035 Uiso 1 1 calc R U . . .
C14 C 0.7962(8) 0.4848(3) 0.1496(2) 0.0260(9) Uani 1 1 d . . . . .
C15 C 0.5770(9) 0.4957(4) 0.1080(3) 0.0361(11) Uani 1 1 d . . . . .
H15 H 0.4435 0.4379 0.0910 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5445(10) 0.5894(4) 0.0898(3) 0.0393(12) Uani 1 1 d . . . . .
H16 H 0.3906 0.5955 0.0611 0.047 Uiso 1 1 calc R U . . .
C17 C 0.7384(10) 0.6727(4) 0.1139(3) 0.0389(12) Uani 1 1 d . . . . .
H17 H 0.7198 0.7366 0.1012 0.047 Uiso 1 1 calc R U . . .
C18 C 0.9581(11) 0.6639(4) 0.1563(3) 0.0460(13) Uani 1 1 d . . . . .
H18 H 1.0910 0.7219 0.1734 0.055 Uiso 1 1 calc R U . . .
C19 C 0.9876(9) 0.5701(4) 0.1743(3) 0.0341(11) Uani 1 1 d . . . . .
H19 H 1.1405 0.5645 0.2039 0.041 Uiso 1 1 calc R U . . .
C20 C 0.8608(7) 0.1959(3) 0.3843(2) 0.0228(9) Uani 1 1 d . . . . .
H20 H 1.0459 0.2054 0.3847 0.027 Uiso 1 1 calc R U . . .
C21 C 0.8241(8) 0.2075(3) 0.4687(2) 0.0257(9) Uani 1 1 d . . . . .
C22 C 0.9968(9) 0.2770(4) 0.5270(3) 0.0335(11) Uani 1 1 d . . . . .
H22 H 1.1404 0.3146 0.5147 0.040 Uiso 1 1 calc R U . . .
C23 C 0.9609(10) 0.2921(4) 0.6042(3) 0.0428(13) Uani 1 1 d . . . . .
H23 H 1.0785 0.3409 0.6438 0.051 Uiso 1 1 calc R U . . .
C24 C 0.7571(10) 0.2368(4) 0.6227(3) 0.0401(12) Uani 1 1 d . . . . .
H24 H 0.7336 0.2468 0.6751 0.048 Uiso 1 1 calc R U . . .
C25 C 0.5875(11) 0.1670(4) 0.5654(3) 0.0455(13) Uani 1 1 d . . . . .
H25 H 0.4460 0.1289 0.5784 0.055 Uiso 1 1 calc R U . . .
C26 C 0.6190(9) 0.1508(4) 0.4880(3) 0.0395(12) Uani 1 1 d . . . . .
H26 H 0.5009 0.1015 0.4489 0.047 Uiso 1 1 calc R U . . .
C27 C 0.7507(7) 0.0883(3) 0.3343(2) 0.0243(9) Uani 1 1 d . . . . .
C28 C 0.8857(8) 0.0075(4) 0.3363(3) 0.0309(10) Uani 1 1 d . . . . .
H28 H 1.0425 0.0205 0.3699 0.037 Uiso 1 1 calc R U . . .
C29 C 0.7931(9) -0.0913(4) 0.2898(3) 0.0367(11) Uani 1 1 d . . . . .
H29 H 0.8879 -0.1452 0.2914 0.044 Uiso 1 1 calc R U . . .
C30 C 0.5673(9) -0.1119(4) 0.2416(3) 0.0366(11) Uani 1 1 d . . . . .
H30 H 0.5057 -0.1797 0.2095 0.044 Uiso 1 1 calc R U . . .
C31 C 0.4288(8) -0.0335(3) 0.2400(3) 0.0322(10) Uani 1 1 d . . . . .
H31 H 0.2703 -0.0477 0.2071 0.039 Uiso 1 1 calc R U . . .
C32 C 0.5200(8) 0.0660(3) 0.2861(3) 0.0277(10) Uani 1 1 d . . . . .
H32 H 0.4230 0.1192 0.2846 0.033 Uiso 1 1 calc R U . . .
C33 C 0.3606(9) 0.4907(4) 0.3904(3) 0.0327(10) Uani 1 1 d . . . . .
H33A H 0.3285 0.4718 0.4382 0.049 Uiso 1 1 calc R U . . .
H33B H 0.2012 0.4815 0.3553 0.049 Uiso 1 1 calc R U . . .
H33C H 0.4440 0.5634 0.4024 0.049 Uiso 1 1 calc R U . . .
C34 C 0.9661(7) 0.1497(4) 0.1964(3) 0.0282(10) Uani 1 1 d . . . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C34 N1 C1 137.1(4) . . ?
C2 C1 C6 122.4(4) . . ?
C2 C1 N1 118.8(4) . . ?
C6 C1 N1 118.7(4) . . ?
C1 C2 C3 117.9(4) . . ?
C1 C2 C7 119.3(4) . . ?
C3 C2 C7 122.9(4) . . ?
C2 C3 C4 121.8(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C33 121.3(4) . . ?
C3 C4 C33 120.4(4) . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C8 C7 C2 113.0(3) . . ?
C8 C7 C14 111.9(3) . . ?
C2 C7 C14 112.9(3) . . ?
C8 C7 H7 106.1 . . ?
C2 C7 H7 106.1 . . ?
C14 C7 H7 106.1 . . ?
C5 C6 C1 117.8(4) . . ?
C5 C6 C20 122.9(4) . . ?
C1 C6 C20 119.3(4) . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C8 C13 118.3(4) . . ?
C9 C8 C7 122.5(4) . . ?
C13 C8 C7 119.2(4) . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C15 C14 C19 118.3(4) . . ?
C15 C14 C7 122.0(4) . . ?
C19 C14 C7 119.7(4) . . ?
C14 C15 C16 121.8(5) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 119.0(5) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.2(5) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.6(4) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C27 C20 C6 112.0(3) . . ?
C27 C20 C21 112.4(3) . . ?
C6 C20 C21 112.2(3) . . ?
C27 C20 H20 106.6 . . ?
C6 C20 H20 106.6 . . ?
C21 C20 H20 106.6 . . ?
C22 C21 C26 119.1(4) . . ?
C22 C21 C20 119.4(4) . . ?
C26 C21 C20 121.5(4) . . ?
C21 C22 C23 120.3(5) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.3(5) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.6(5) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 121.1(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 119.6(5) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C32 C27 C28 118.1(4) . . ?
C32 C27 C20 122.7(4) . . ?
C28 C27 C20 119.2(4) . . ?
C29 C28 C27 120.7(4) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C30 C29 C28 120.7(4) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.5(4) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C30 C31 C32 120.4(4) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C27 C32 C31 120.7(4) . . ?
C27 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C4 C33 H33A 109.5 . . ?
C4 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C4 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O1 C34 N1 172.2(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C34 1.170(6) . ?
N1 C34 1.200(6) . ?
N1 C1 1.421(5) . ?
C1 C2 1.392(6) . ?
C1 C6 1.398(6) . ?
C2 C3 1.393(6) . ?
C2 C7 1.530(6) . ?
C3 C4 1.398(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(6) . ?
C4 C33 1.517(6) . ?
C5 C6 1.393(6) . ?
C5 H5 0.9500 . ?
C7 C8 1.516(6) . ?
C7 C14 1.537(6) . ?
C7 H7 1.0000 . ?
C6 C20 1.529(6) . ?
C9 C8 1.389(6) . ?
C9 C10 1.402(6) . ?
C9 H9 0.9500 . ?
C8 C13 1.399(6) . ?
C10 C11 1.385(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.369(6) . ?
C14 C19 1.383(6) . ?
C15 C16 1.395(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.368(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C27 1.513(6) . ?
C20 C21 1.535(6) . ?
C20 H20 1.0000 . ?
C21 C22 1.384(6) . ?
C21 C26 1.390(7) . ?
C22 C23 1.402(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.369(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.369(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.385(6) . ?
C27 C28 1.398(6) . ?
C28 C29 1.387(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.364(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.384(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(6) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
