#------------------------------------------------------------------------------
#$Date: 2022-01-02 10:39:39 +0200 (Sun, 02 Jan 2022) $
#$Revision: 271679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/60/4036001.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_4036001
loop_
_publ_author_name
'Gawade, Prashant M.'
'Khose, Vaibhav N.'
'Badani, Purav M.'
'Hasan, Mohammed'
'Kaabel, Sandra'
'Mobin, Shaikh M.'
'Borovkov, Victor'
'Karnik, Anil V.'
_publ_section_title
;
 Benzyne-Mediated Nonconcerted Pathway toward Synthesis of Sterically
 Crowded [5]- and [7]Oxahelicenoids, Stereochemical and Theoretical
 Studies, and Optical Resolution of Helicenoids.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              860
_journal_page_last               868
_journal_paper_doi               10.1021/acs.joc.8b02507
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C32 H20 Br2 O2'
_chemical_formula_weight         596.30
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'A e a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2662(2)
_cell_length_b                   15.6756(2)
_cell_length_c                   14.1746(3)
_cell_measurement_reflns_used    5393
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.9910
_cell_measurement_theta_min      3.9470
_cell_volume                     2503.30(8)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7638
_diffrn_reflns_theta_full        71.32
_diffrn_reflns_theta_max         71.32
_diffrn_reflns_theta_min         5.64
_exptl_absorpt_coefficient_mu    4.330
_exptl_absorpt_correction_T_max  0.5824
_exptl_absorpt_correction_T_min  0.4358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0954P)²+1.5163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                1988
_reflns_number_total             2043
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02507_si_004.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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 6909 2019-04-08 15:41:33Z antanas 

2022-01-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42.67 H26.67 Br2.67 O2.67'
_cod_original_formula_weight         795.07
_cod_original_formula_units_Z            3
_cod_original_sg_symbol_H-M      'A b a 2'
_cod_database_code               4036001
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.26071(6) 0.35258(3) 0.10296(8) 0.0779(3) Uani 1 1 d .
O1 O 0.7322(3) 0.3632(3) 0.5451(4) 0.0646(10) Uani 1 1 d .
C1 C 0.5220(5) 0.4591(5) 0.8955(4) 0.0808(16) Uani 1 1 d .
H1 H 0.5347 0.4302 0.9536 0.097 Uiso 1 1 calc R
C2 C 0.5478(4) 0.4191(4) 0.8114(4) 0.0671(12) Uani 1 1 d .
H2 H 0.5814 0.3636 0.8118 0.080 Uiso 1 1 calc R
C3 C 0.5246(3) 0.4599(3) 0.7249(3) 0.0518(9) Uani 1 1 d .
C4 C 0.5572(3) 0.4155(2) 0.6350(3) 0.0476(8) Uani 1 1 d .
H4 H 0.5210 0.3573 0.6356 0.057 Uiso 1 1 calc R
C5 C 0.5217(3) 0.4597(2) 0.5443(3) 0.0394(7) Uani 1 1 d .
C6 C 0.5516(3) 0.40449(19) 0.4627(3) 0.0412(8) Uani 1 1 d .
C7 C 0.4809(3) 0.39163(17) 0.3815(3) 0.0383(8) Uani 1 1 d .
C8 C 0.3647(3) 0.42580(19) 0.3707(3) 0.0423(7) Uani 1 1 d .
H8 H 0.3312 0.4581 0.4208 0.051 Uiso 1 1 calc R
C9 C 0.3003(4) 0.4137(2) 0.2912(3) 0.0471(8) Uani 1 1 d .
H9 H 0.2228 0.4372 0.2861 0.057 Uiso 1 1 calc R
C10 C 0.3484(4) 0.3662(2) 0.2157(3) 0.0506(9) Uani 1 1 d .
C11 C 0.4576(4) 0.3289(2) 0.2232(4) 0.0563(10) Uani 1 1 d .
H11 H 0.4887 0.2967 0.1721 0.068 Uiso 1 1 calc R
C12 C 0.5235(3) 0.3384(2) 0.3059(3) 0.0467(9) Uani 1 1 d .
C13 C 0.6329(4) 0.2950(2) 0.3189(4) 0.0536(9) Uani 1 1 d .
H13 H 0.6622 0.2595 0.2698 0.064 Uiso 1 1 calc R
C14 C 0.6958(4) 0.3029(2) 0.3983(4) 0.0550(11) Uani 1 1 d .
H14 H 0.7667 0.2710 0.4062 0.066 Uiso 1 1 calc R
C15 C 0.6575(4) 0.3585(2) 0.4707(3) 0.0478(9) Uani 1 1 d .
C16 C 0.6928(4) 0.4060(3) 0.6297(3) 0.0572(10) Uani 1 1 d .
H16A H 0.7296 0.4633 0.6323 0.069 Uiso 1 1 calc R
H16B H 0.7206 0.3735 0.6853 0.069 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C15 O1 C16 118.9(3) .
C1 C1 C2 120.0(3) 2_665
C1 C1 H1 120.0 2_665
C2 C1 H1 120.0 .
C1 C2 C3 120.5(5) .
C1 C2 H2 119.7 .
C3 C2 H2 119.7 .
C3 C3 C2 119.4(3) 2_665
C3 C3 C4 121.6(2) 2_665
C2 C3 C4 119.0(4) .
C3 C4 C5 116.5(3) .
C3 C4 C16 109.3(3) .
C5 C4 C16 105.4(3) .
C3 C4 H4 108.5 .
C5 C4 H4 108.5 .
C16 C4 H4 108.5 .
C5 C5 C6 128.74(19) 2_665
C5 C5 C4 121.42(19) 2_665
C6 C5 C4 109.7(3) .
C15 C6 C7 118.2(3) .
C15 C6 C5 115.5(3) .
C7 C6 C5 126.2(3) .
C6 C7 C8 123.5(3) .
C6 C7 C12 120.0(3) .
C8 C7 C12 116.4(3) .
C9 C8 C7 122.0(4) .
C9 C8 H8 119.0 .
C7 C8 H8 119.0 .
C8 C9 C10 120.0(4) .
C8 C9 H9 120.0 .
C10 C9 H9 120.0 .
C11 C10 C9 120.8(4) .
C11 C10 Br1 119.2(4) .
C9 C10 Br1 120.0(3) .
C10 C11 C12 119.9(4) .
C10 C11 H11 120.0 .
C12 C11 H11 120.0 .
C11 C12 C13 121.3(4) .
C11 C12 C7 120.6(3) .
C13 C12 C7 118.1(4) .
C14 C13 C12 121.6(4) .
C14 C13 H13 119.2 .
C12 C13 H13 119.2 .
C13 C14 C15 120.5(4) .
C13 C14 H14 119.7 .
C15 C14 H14 119.7 .
O1 C15 C6 124.5(4) .
O1 C15 C14 114.3(4) .
C6 C15 C14 121.2(4) .
O1 C16 C4 113.0(4) .
O1 C16 H16A 109.0 .
C4 C16 H16A 109.0 .
O1 C16 H16B 109.0 .
C4 C16 H16B 109.0 .
H16A C16 H16B 107.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C10 1.891(5) .
O1 C15 1.351(6) .
O1 C16 1.444(7) .
C1 C1 1.373(14) 2_665
C1 C2 1.379(8) .
C1 H1 0.9500 .
C2 C3 1.407(6) .
C2 H2 0.9500 .
C3 C3 1.374(9) 2_665
C3 C4 1.497(6) .
C4 C5 1.514(5) .
C4 C16 1.537(6) .
C4 H4 1.0000 .
C5 C5 1.356(7) 2_665
C5 C6 1.483(5) .
C6 C15 1.399(5) .
C6 C7 1.414(5) .
C7 C8 1.423(5) .
C7 C12 1.440(5) .
C8 C9 1.354(6) .
C8 H8 0.9500 .
C9 C10 1.411(6) .
C9 H9 0.9500 .
C10 C11 1.366(7) .
C11 C12 1.396(7) .
C11 H11 0.9500 .
C12 C13 1.419(6) .
C13 C14 1.336(7) .
C13 H13 0.9500 .
C14 C15 1.413(6) .
C14 H14 0.9500 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
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_4
C1 C1 C2 C3 -2.7(10) 2_665 .
C1 C2 C3 C3 -0.3(8) . 2_665
C1 C2 C3 C4 178.1(5) . .
C3 C3 C4 C5 -6.0(7) 2_665 .
C2 C3 C4 C5 175.6(4) . .
C3 C3 C4 C16 113.2(5) 2_665 .
C2 C3 C4 C16 -65.2(5) . .
C3 C4 C5 C5 9.1(6) . 2_665
C16 C4 C5 C5 -112.3(5) . 2_665
C3 C4 C5 C6 -175.5(3) . .
C16 C4 C5 C6 63.2(4) . .
C5 C5 C6 C15 137.5(5) 2_665 .
C4 C5 C6 C15 -37.5(4) . .
C5 C5 C6 C7 -45.6(6) 2_665 .
C4 C5 C6 C7 139.3(3) . .
C15 C6 C7 C8 171.5(3) . .
C5 C6 C7 C8 -5.2(5) . .
C15 C6 C7 C12 -5.5(5) . .
C5 C6 C7 C12 177.7(3) . .
C6 C7 C8 C9 178.6(3) . .
C12 C7 C8 C9 -4.2(5) . .
C7 C8 C9 C10 -0.2(6) . .
C8 C9 C10 C11 2.8(6) . .
C8 C9 C10 Br1 -177.8(3) . .
C9 C10 C11 C12 -0.6(6) . .
Br1 C10 C11 C12 180.0(3) . .
C10 C11 C12 C13 174.9(4) . .
C10 C11 C12 C7 -4.1(6) . .
C6 C7 C12 C11 -176.4(3) . .
C8 C7 C12 C11 6.3(5) . .
C6 C7 C12 C13 4.6(5) . .
C8 C7 C12 C13 -172.7(3) . .
C11 C12 C13 C14 -179.2(4) . .
C7 C12 C13 C14 -0.2(6) . .
C12 C13 C14 C15 -3.1(6) . .
C16 O1 C15 C6 11.5(7) . .
C16 O1 C15 C14 -169.4(4) . .
C7 C6 C15 O1 -178.6(4) . .
C5 C6 C15 O1 -1.5(6) . .
C7 C6 C15 C14 2.3(5) . .
C5 C6 C15 C14 179.4(3) . .
C13 C14 C15 O1 -177.1(4) . .
C13 C14 C15 C6 2.0(6) . .
C15 O1 C16 C4 18.6(6) . .
C3 C4 C16 O1 179.6(4) . .
C5 C4 C16 O1 -54.5(4) . .
