#------------------------------------------------------------------------------
#$Date: 2021-11-03 00:55:54 +0200 (Wed, 03 Nov 2021) $
#$Revision: 270209 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129179.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_7129179
loop_
_publ_author_name
'Mandal, Rajib'
'Barsu, Nagaraju'
'Garai, Bholanath'
'Das, Abir'
'Perekalin, Dmitry'
'Sundararaju, Basker'
_publ_section_title
;
 Room-temperature C--H bond alkynylation by merging cobalt and
 photocatalysts
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05263B
_journal_year                    2021
_chemical_formula_moiety         'C31 H36 N2 O3'
_chemical_formula_sum            'C31 H36 N2 O3'
_chemical_formula_weight         484.62
_chemical_name_systematic        5AC
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-16 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                106.492(2)
_cell_angle_beta                 95.327(2)
_cell_angle_gamma                97.944(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2757(6)
_cell_length_b                   12.3903(9)
_cell_length_c                   13.7007(10)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    273
_cell_measurement_theta_max      28.317
_cell_measurement_theta_min      2.510
_cell_volume                     1321.16(17)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_min         2.509
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1009 before and 0.0646 after correction. The Ratio of minimum to maximum transmission is 0.8647. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_preparation       'Cobalt cataluzed annulation'
_exptl_crystal_recrystallization_method
'Slow Evaporation in dichloromethane solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0483
_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)+(0.0347P)²+0.9323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5179
_reflns_number_total             6569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc05263b2.cif
_cod_data_source_block           24auga_0m
_cod_database_code               7129179
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_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.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C26(H26A,H26B), C25(H25A,H25B), C29(H29A,H29B), C28(H28A,
 H28B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C12(H12), C15(H15), C16(H16), C17(H17), C6(H6), C4(H4),
 C5(H5)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C22(H22A,H22B,
 H22C), C21(H21A,H21B,H21C)
;
_olex2_submission_original_sample_id BSRM-3890
_olex2_submission_special_instructions 'No special instructions were received'
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
O2 O 0.37156(12) 0.67341(8) 0.70666(7) 0.0165(2) Uani 1 1 d . . . . .
O3 O 0.10729(13) 0.67905(9) 0.73219(8) 0.0237(2) Uani 1 1 d . . . . .
O1 O 0.31439(14) 0.31446(9) 0.74313(8) 0.0244(2) Uani 1 1 d . . . . .
N1 N 0.32686(14) 0.48831(10) 0.71918(8) 0.0151(2) Uani 1 1 d . . . . .
N2 N 0.64759(15) 0.57840(11) 0.81276(9) 0.0193(3) Uani 1 1 d . . . . .
C9 C 0.33084(16) 0.55737(11) 0.65505(10) 0.0150(3) Uani 1 1 d . . . . .
C18 C 0.52654(17) 0.58647(11) 0.87440(10) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.27743(16) 0.39423(12) 0.50684(10) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.30799(16) 0.51726(12) 0.55221(10) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.36090(17) 0.54019(11) 0.82912(10) 0.0157(3) Uani 1 1 d . . . . .
C14 C 0.55832(18) 0.64022(12) 0.98241(10) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.27389(16) 0.32044(12) 0.56939(10) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.30568(17) 0.36950(12) 0.68174(10) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.23581(18) 0.54485(12) 0.88761(11) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.128021 0.514211 0.856573 0.022 Uiso 1 1 calc R . . . .
C19 C 0.24543(17) 0.72813(12) 0.74301(10) 0.0172(3) Uani 1 1 d . . . . .
C24 C 0.31383(17) 0.59649(12) 0.48653(11) 0.0172(3) Uani 1 1 d . . . . .
H24A H 0.376941 0.568621 0.431225 0.021 Uiso 1 1 calc R . . . .
H24B H 0.371425 0.671484 0.527986 0.021 Uiso 1 1 calc R . . . .
C13 C 0.42682(19) 0.64285(12) 1.04184(11) 0.0202(3) Uani 1 1 d . . . . .
H13 H 0.447708 0.676464 1.112689 0.024 Uiso 1 1 calc R . . . .
C3 C 0.24349(17) 0.20013(12) 0.52355(11) 0.0186(3) Uani 1 1 d . . . . .
C12 C 0.26955(19) 0.59616(13) 0.99533(11) 0.0214(3) Uani 1 1 d . . . . .
H12 H 0.183814 0.598090 1.034795 0.026 Uiso 1 1 calc R . . . .
C15 C 0.72335(19) 0.68919(13) 1.02603(11) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.749907 0.725541 1.096287 0.026 Uiso 1 1 calc R . . . .
C16 C 0.84309(19) 0.68221(14) 0.96323(12) 0.0252(3) Uani 1 1 d . . . . .
H16 H 0.952142 0.714541 0.990050 0.030 Uiso 1 1 calc R . . . .
C26 C 0.15509(18) 0.66386(12) 0.35338(11) 0.0194(3) Uani 1 1 d . . . . .
H26A H 0.215309 0.620853 0.302770 0.023 Uiso 1 1 calc R . . . .
H26B H 0.044839 0.659243 0.319723 0.023 Uiso 1 1 calc R . . . .
C17 C 0.79892(19) 0.62527(14) 0.85713(12) 0.0237(3) Uani 1 1 d . . . . .
H17 H 0.882309 0.620542 0.815812 0.028 Uiso 1 1 calc R . . . .
C25 C 0.14340(17) 0.60848(13) 0.43972(11) 0.0189(3) Uani 1 1 d . . . . .
H25A H 0.075057 0.533481 0.412783 0.023 Uiso 1 1 calc R . . . .
H25B H 0.090890 0.654521 0.493171 0.023 Uiso 1 1 calc R . . . .
C6 C 0.25452(17) 0.34651(13) 0.39927(11) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.259686 0.394071 0.357537 0.023 Uiso 1 1 calc R . . . .
C29 C 0.13295(19) 0.84208(13) 0.23062(12) 0.0234(3) Uani 1 1 d . . . . .
H29A H 0.054924 0.880793 0.269956 0.028 Uiso 1 1 calc R . . . .
H29B H 0.078739 0.764513 0.194202 0.028 Uiso 1 1 calc R . . . .
C28 C 0.28107(19) 0.83881(13) 0.30408(11) 0.0218(3) Uani 1 1 d . . . . .
H28A H 0.341059 0.916085 0.334655 0.026 Uiso 1 1 calc R . . . .
H28B H 0.353796 0.794351 0.264619 0.026 Uiso 1 1 calc R . . . .
C4 C 0.21731(19) 0.15813(13) 0.41721(11) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.194189 0.079515 0.386045 0.027 Uiso 1 1 calc R . . . .
C20 C 0.30942(19) 0.85427(12) 0.79473(11) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.22470(19) 0.23048(13) 0.35580(11) 0.0233(3) Uani 1 1 d . . . . .
H5 H 0.209227 0.199671 0.284630 0.028 Uiso 1 1 calc R . . . .
C27 C 0.23983(19) 0.78862(13) 0.39041(11) 0.0221(3) Uani 1 1 d . . . . .
H27A H 0.340915 0.795039 0.435175 0.027 Uiso 1 1 calc R . . . .
H27B H 0.168880 0.833843 0.430864 0.027 Uiso 1 1 calc R . . . .
C23 C 0.4590(2) 0.86902(14) 0.87557(12) 0.0276(3) Uani 1 1 d . . . . .
H23A H 0.426370 0.834920 0.927038 0.041 Uiso 1 1 calc GR . . . .
H23B H 0.500792 0.948930 0.907184 0.041 Uiso 1 1 calc GR . . . .
H23C H 0.543288 0.832429 0.843004 0.041 Uiso 1 1 calc GR . . . .
C31 C 0.2392(2) 0.11532(13) 0.58366(12) 0.0255(3) Uani 1 1 d . . . . .
H31A H 0.346442 0.122957 0.620864 0.038 Uiso 1 1 calc GR . . . .
H31B H 0.207753 0.039249 0.537249 0.038 Uiso 1 1 calc GR . . . .
H31C H 0.160746 0.129715 0.631151 0.038 Uiso 1 1 calc GR . . . .
C30 C 0.1816(2) 0.90327(14) 0.15269(12) 0.0275(3) Uani 1 1 d . . . . .
H30A H 0.084634 0.905432 0.109529 0.041 Uiso 1 1 calc GR . . . .
H30B H 0.254460 0.862980 0.111161 0.041 Uiso 1 1 calc GR . . . .
H30C H 0.236432 0.979852 0.188376 0.041 Uiso 1 1 calc GR . . . .
C22 C 0.3604(2) 0.90763(14) 0.71165(13) 0.0320(4) Uani 1 1 d . . . . .
H22A H 0.447731 0.873028 0.681049 0.048 Uiso 1 1 calc GR . . . .
H22B H 0.397802 0.988249 0.742090 0.048 Uiso 1 1 calc GR . . . .
H22C H 0.267622 0.895021 0.659774 0.048 Uiso 1 1 calc GR . . . .
C21 C 0.1730(2) 0.90975(15) 0.84583(16) 0.0382(4) Uani 1 1 d . . . . .
H21A H 0.081244 0.901884 0.794557 0.057 Uiso 1 1 calc GR . . . .
H21B H 0.213639 0.989344 0.879953 0.057 Uiso 1 1 calc GR . . . .
H21C H 0.138356 0.872945 0.895144 0.057 Uiso 1 1 calc GR . . . .
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
C19 O2 C9 116.90(11) . . ?
C9 N1 C10 119.51(11) . . ?
C9 N1 C1 122.57(11) . . ?
C1 N1 C10 117.67(11) . . ?
C17 N2 C18 117.10(12) . . ?
O2 C9 N1 114.07(11) . . ?
C8 C9 O2 121.90(12) . . ?
C8 C9 N1 123.91(12) . . ?
N2 C18 C10 118.90(12) . . ?
N2 C18 C14 122.98(13) . . ?
C10 C18 C14 118.12(12) . . ?
C2 C7 C8 120.97(12) . . ?
C6 C7 C8 119.92(12) . . ?
C6 C7 C2 119.09(12) . . ?
C9 C8 C7 117.04(12) . . ?
C9 C8 C24 121.53(12) . . ?
C7 C8 C24 121.43(12) . . ?
C18 C10 N1 118.53(12) . . ?
C11 C10 N1 120.35(13) . . ?
C11 C10 C18 121.11(13) . . ?
C13 C14 C18 119.80(13) . . ?
C15 C14 C18 117.51(13) . . ?
C15 C14 C13 122.69(13) . . ?
C7 C2 C1 119.50(12) . . ?
C7 C2 C3 120.16(12) . . ?
C3 C2 C1 120.32(12) . . ?
O1 C1 N1 118.91(12) . . ?
O1 C1 C2 125.24(13) . . ?
N1 C1 C2 115.85(11) . . ?
C10 C11 C12 120.21(14) . . ?
O2 C19 C20 110.24(12) . . ?
O3 C19 O2 122.35(13) . . ?
O3 C19 C20 127.41(13) . . ?
C8 C24 C25 114.10(11) . . ?
C12 C13 C14 120.14(13) . . ?
C2 C3 C31 123.89(13) . . ?
C4 C3 C2 118.11(13) . . ?
C4 C3 C31 118.01(13) . . ?
C13 C12 C11 120.59(13) . . ?
C16 C15 C14 118.95(13) . . ?
C15 C16 C17 119.09(14) . . ?
C27 C26 C25 113.57(12) . . ?
N2 C17 C16 124.36(14) . . ?
C26 C25 C24 111.98(11) . . ?
C5 C6 C7 120.30(13) . . ?
C28 C29 C30 112.27(13) . . ?
C29 C28 C27 115.12(13) . . ?
C3 C4 C5 121.75(13) . . ?
C19 C20 C23 109.60(12) . . ?
C19 C20 C22 107.81(12) . . ?
C19 C20 C21 109.12(13) . . ?
C22 C20 C23 109.93(13) . . ?
C21 C20 C23 110.02(14) . . ?
C21 C20 C22 110.32(14) . . ?
C6 C5 C4 120.55(13) . . ?
C26 C27 C28 114.25(12) . . ?
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
O2 C9 1.3876(16) . ?
O2 C19 1.3776(17) . ?
O3 C19 1.1933(17) . ?
O1 C1 1.2271(16) . ?
N1 C9 1.3891(17) . ?
N1 C10 1.4432(17) . ?
N1 C1 1.3943(17) . ?
N2 C18 1.3651(18) . ?
N2 C17 1.3162(19) . ?
C9 C8 1.3398(19) . ?
C18 C10 1.4197(19) . ?
C18 C14 1.4221(19) . ?
C7 C8 1.4492(19) . ?
C7 C2 1.4189(18) . ?
C7 C6 1.4072(19) . ?
C8 C24 1.5075(18) . ?
C10 C11 1.3643(19) . ?
C14 C13 1.417(2) . ?
C14 C15 1.416(2) . ?
C2 C1 1.4688(19) . ?
C2 C3 1.4196(19) . ?
C11 C12 1.415(2) . ?
C19 C20 1.516(2) . ?
C24 C25 1.5384(19) . ?
C13 C12 1.365(2) . ?
C3 C4 1.386(2) . ?
C3 C31 1.507(2) . ?
C15 C16 1.367(2) . ?
C16 C17 1.411(2) . ?
C26 C25 1.5308(19) . ?
C26 C27 1.526(2) . ?
C6 C5 1.368(2) . ?
C29 C28 1.525(2) . ?
C29 C30 1.527(2) . ?
C28 C27 1.528(2) . ?
C4 C5 1.392(2) . ?
C20 C23 1.536(2) . ?
C20 C22 1.533(2) . ?
C20 C21 1.525(2) . ?
