#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:35:16 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296673 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160147.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_7160147
loop_
_publ_author_name
'Varalaxmi, Kasarla'
'Pradhan, Kangkan'
'Begam, Hasina Mamataj'
'Polley, Arghya'
'Kumar, Deepak'
'Jana, Ranjan'
_publ_section_title
;
 Transition-metal-free iterative two-fold reductive coupling and
 1,3-borotropic shift to form 1,4-skipped dienes.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8596
_journal_page_last               8601
_journal_paper_doi               10.1039/d4ob01389a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H30'
_chemical_formula_sum            'C20 H30'
_chemical_formula_weight         270.461
_chemical_name_systematic        KVL-112
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2f3rlx
_audit_creation_date             2022-12-26
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-25 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.293(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2632(6)
_cell_length_b                   24.832(3)
_cell_length_c                   11.5592(12)
_cell_measurement_reflns_used    7770
_cell_measurement_temperature    115.0
_cell_measurement_theta_max      64.615
_cell_measurement_theta_min      3.560
_cell_volume                     1783.2(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_temperature      115.0
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.9921
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1617
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.9921
_diffrn_reflns_Laue_measured_fraction_max 0.9921
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23023
_diffrn_reflns_point_group_measured_fraction_full 0.9921
_diffrn_reflns_point_group_measured_fraction_max 0.9921
_diffrn_reflns_theta_full        64.9739
_diffrn_reflns_theta_max         64.97
_diffrn_reflns_theta_min         3.56
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1214 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.8659.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.007
_exptl_crystal_description       block
_exptl_crystal_F_000             601.535
_exptl_crystal_preparation       CHCl3
_exptl_crystal_recrystallization_method CHCl3
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.4397
_refine_diff_density_min         -0.3577
_refine_diff_density_rms         0.0701
_refine_ls_d_res_high            0.8508
_refine_ls_d_res_low             12.4158
_refine_ls_goodness_of_fit_ref   1.0375
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0375
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1331P)²+0.5349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2079
_refine_ls_wR_factor_ref         0.2146
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              -5
_reflns_number_gt                2647
_reflns_number_total             3022
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob01389a2.cif
_cod_data_source_block           kvl_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160147.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7160147
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C8(H8), C2(H2), C3(H3), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C20(H20a,H20b,H20c), C18(H18a,H18b,H18c), C19(H19a,H19b,
 H19c), C17(H17a,H17b,H17c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
;
_olex2_exptl_crystal_mounting_method 'CRYSTAL WAS MOUNTED'
_olex2_submission_original_sample_id KVL-112
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
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_refinement_flags_posn
C1 C 0.3658(3) 0.56926(7) 0.63455(15) 0.0332(5) Uani 1.000000 .
C7 C 0.5150(3) 0.69490(8) 0.39857(16) 0.0360(5) Uani 1.000000 .
H7 H 0.3962(3) 0.71256(8) 0.35519(16) 0.0432(6) Uiso 1.000000 R
C4 C 0.4661(3) 0.65329(7) 0.48142(16) 0.0334(5) Uani 1.000000 .
C10 C 0.8829(3) 0.72613(8) 0.19930(17) 0.0388(5) Uani 1.000000 .
H10 H 0.9463(3) 0.75022(8) 0.14970(17) 0.0465(6) Uiso 1.000000 R
C11 C 0.9039(3) 0.67402(8) 0.17759(16) 0.0377(5) Uani 1.000000 .
H11 H 0.8445(3) 0.64920(8) 0.22728(16) 0.0453(6) Uiso 1.000000 R
C8 C 0.7095(3) 0.71003(8) 0.37886(16) 0.0366(5) Uani 1.000000 .
H8 H 0.8263(3) 0.69237(8) 0.42400(16) 0.0439(6) Uiso 1.000000 R
C2 C 0.5651(3) 0.59492(8) 0.64793(16) 0.0372(5) Uani 1.000000 .
H2 H 0.6706(3) 0.58406(8) 0.70993(16) 0.0447(6) Uiso 1.000000 R
C14 C 0.3184(3) 0.52200(8) 0.71265(16) 0.0367(5) Uani 1.000000 .
C3 C 0.6151(3) 0.63560(8) 0.57434(16) 0.0371(5) Uani 1.000000 .
H3 H 0.7534(3) 0.65190(8) 0.58701(16) 0.0446(6) Uiso 1.000000 R
C6 C 0.2162(3) 0.58767(8) 0.54346(17) 0.0394(5) Uani 1.000000 .
H6 H 0.0772(3) 0.57175(8) 0.53184(17) 0.0473(6) Uiso 1.000000 R
C5 C 0.2648(3) 0.62867(8) 0.46921(17) 0.0384(5) Uani 1.000000 .
H5 H 0.1579(3) 0.64018(8) 0.40855(17) 0.0461(6) Uiso 1.000000 R
C9 C 0.7697(3) 0.75173(8) 0.29390(16) 0.0386(5) Uani 1.000000 .
C12 C 1.0144(3) 0.65137(8) 0.08036(17) 0.0408(5) Uani 1.000000 .
H12 H 1.0537(3) 0.68196(8) 0.03091(17) 0.0489(6) Uiso 1.000000 R
C13 C 0.5748(3) 0.78329(9) 0.23490(19) 0.0477(6) Uani 1.000000 .
H13a H 0.6233(4) 0.8103(4) 0.1822(11) 0.0715(9) Uiso 1.000000 GR
H13b H 0.4743(13) 0.75843(13) 0.1903(11) 0.0715(9) Uiso 1.000000 GR
H13c H 0.5023(16) 0.8013(5) 0.2945(2) 0.0715(9) Uiso 1.000000 GR
C20 C 0.9289(4) 0.79177(9) 0.36176(19) 0.0478(6) Uani 1.000000 .
H20a H 1.0511(13) 0.77188(11) 0.4026(11) 0.0717(8) Uiso 1.000000 GR
H20b H 0.981(2) 0.8173(4) 0.3070(3) 0.0717(8) Uiso 1.000000 GR
H20c H 0.8554(8) 0.8115(5) 0.4186(10) 0.0717(8) Uiso 1.000000 GR
C18 C 1.2211(3) 0.62164(9) 0.12796(19) 0.0486(6) Uani 1.000000 .
H18a H 1.3198(11) 0.64669(19) 0.1732(12) 0.0729(9) Uiso 1.000000 GR
H18b H 1.1861(5) 0.5920(4) 0.1783(12) 0.0729(9) Uiso 1.000000 GR
H18c H 1.2896(14) 0.6072(6) 0.0629(2) 0.0729(9) Uiso 1.000000 GR
C19 C 0.8642(4) 0.61376(9) 0.00411(19) 0.0523(6) Uani 1.000000 .
H19a H 0.824(2) 0.5834(4) 0.0511(4) 0.0784(9) Uiso 1.000000 GR
H19b H 0.7344(13) 0.6335(2) -0.0278(12) 0.0784(9) Uiso 1.000000 GR
H19c H 0.9376(11) 0.6002(6) -0.0600(9) 0.0784(9) Uiso 1.000000 GR
C17 C 0.3896(5) 0.47002(10) 0.6576(2) 0.0668(8) Uani 1.000000 .
H17a H 0.305(2) 0.4649(4) 0.5809(8) 0.1002(11) Uiso 1.000000 GR
H17b H 0.5427(9) 0.4724(3) 0.6486(16) 0.1002(11) Uiso 1.000000 GR
H17c H 0.366(3) 0.43942(14) 0.7080(9) 0.1002(11) Uiso 1.000000 GR
C15 C 0.0811(4) 0.51778(13) 0.7248(3) 0.0776(9) Uani 1.000000 .
H15a H 0.0317(10) 0.5517(4) 0.7556(19) 0.1165(14) Uiso 1.000000 GR
H15b H -0.0003(6) 0.5106(9) 0.6482(5) 0.1165(14) Uiso 1.000000 GR
H15c H 0.0583(6) 0.4883(6) 0.7783(17) 0.1165(14) Uiso 1.000000 GR
C16 C 0.4435(6) 0.52686(13) 0.8350(2) 0.0804(10) Uani 1.000000 .
H16a H 0.5984(6) 0.5258(10) 0.8297(3) 0.1206(15) Uiso 1.000000 GR
H16b H 0.407(3) 0.5610(5) 0.8703(8) 0.1206(15) Uiso 1.000000 GR
H16c H 0.405(3) 0.4969(5) 0.8835(7) 0.1206(15) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C14 C1 C2 121.52(16) . . ?
C6 C1 C2 116.15(17) . . ?
C6 C1 C14 122.28(16) . . ?
C4 C7 H7 117.07(10) . . ?
C8 C7 H7 117.07(11) . . ?
C8 C7 C4 125.86(17) . . ?
C3 C4 C7 123.18(17) . . ?
C5 C4 C7 120.30(16) . . ?
C5 C4 C3 116.52(17) . . ?
C11 C10 H10 116.15(12) . . ?
C9 C10 H10 116.15(10) . . ?
C9 C10 C11 127.69(18) . . ?
H11 C11 C10 117.54(12) . . ?
C12 C11 C10 124.92(18) . . ?
C12 C11 H11 117.54(11) . . ?
H8 C8 C7 115.86(11) . . ?
C9 C8 C7 128.28(17) . . ?
C9 C8 H8 115.86(10) . . ?
H2 C2 C1 118.79(11) . . ?
C3 C2 C1 122.42(17) . . ?
C3 C2 H2 118.79(10) . . ?
C17 C14 C1 108.21(16) . . ?
C15 C14 C1 111.91(17) . . ?
C15 C14 C17 108.7(2) . . ?
C16 C14 C1 111.66(17) . . ?
C16 C14 C17 108.0(2) . . ?
C16 C14 C15 108.2(2) . . ?
C2 C3 C4 121.34(17) . . ?
H3 C3 C4 119.33(11) . . ?
H3 C3 C2 119.33(10) . . ?
H6 C6 C1 119.09(11) . . ?
C5 C6 C1 121.82(17) . . ?
C5 C6 H6 119.09(10) . . ?
C6 C5 C4 121.72(17) . . ?
H5 C5 C4 119.14(11) . . ?
H5 C5 C6 119.14(10) . . ?
C8 C9 C10 111.12(15) . . ?
C13 C9 C10 108.17(16) . . ?
C13 C9 C8 112.92(16) . . ?
C20 C9 C10 107.72(16) . . ?
C20 C9 C8 108.01(15) . . ?
C20 C9 C13 108.76(17) . . ?
H12 C12 C11 108.27(11) . . ?
C18 C12 C11 111.15(16) . . ?
C18 C12 H12 108.27(12) . . ?
C19 C12 C11 110.66(17) . . ?
C19 C12 H12 108.27(12) . . ?
C19 C12 C18 110.12(18) . . ?
H13a C13 C9 109.5 . . ?
H13b C13 C9 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C9 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H20a C20 C9 109.5 . . ?
H20b C20 C9 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C9 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H18a C18 C12 109.5 . . ?
H18b C18 C12 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C12 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H19a C19 C12 109.5 . . ?
H19b C19 C12 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C12 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H17a C17 C14 109.5 . . ?
H17b C17 C14 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C14 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H15a C15 C14 109.5 . . ?
H15b C15 C14 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C14 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H16a C16 C14 109.5 . . ?
H16b C16 C14 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C14 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
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
C1 C2 1.393(3) . ?
C1 C14 1.532(3) . ?
C1 C6 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C4 1.467(3) . ?
C7 C8 1.322(3) . ?
C4 C3 1.401(3) . ?
C4 C5 1.392(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.328(3) . ?
C10 C9 1.516(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.502(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.507(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C14 C17 1.530(3) . ?
C14 C15 1.514(3) . ?
C14 C16 1.533(3) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C9 C13 1.536(3) . ?
C9 C20 1.549(3) . ?
C12 H12 1.0000 . ?
C12 C18 1.530(3) . ?
C12 C19 1.524(3) . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
C15 H15a 0.9800 . ?
C15 H15b 0.9800 . ?
C15 H15c 0.9800 . ?
C16 H16a 0.9800 . ?
C16 H16b 0.9800 . ?
C16 H16c 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.0(2) . . . . ?
C1 C6 C5 C4 0.4(2) . . . . ?
C7 C4 C3 C2 -177.64(18) . . . . ?
C7 C4 C5 C6 177.47(18) . . . . ?
C7 C8 C9 C10 -114.8(2) . . . . ?
C7 C8 C9 C13 6.9(2) . . . . ?
C7 C8 C9 C20 127.2(2) . . . . ?
C10 C11 C12 C18 112.7(2) . . . . ?
C10 C11 C12 C19 -124.6(2) . . . . ?
