#------------------------------------------------------------------------------
#$Date: 2017-05-18 07:25:17 +0300 (Thu, 18 May 2017) $
#$Revision: 196746 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/56/7155630.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_7155630
loop_
_publ_author_name
'Del Grosso, Alessandro'
'Galanopoulos, Lavrentis-Dimitrios'
'Chiu, Cookson K. C.'
'Clarkson, Guy J.'
'O′ Connor, Peter B.'
'Wills, Martin'
_publ_section_title
;
 Strained alkynes derived from 2,2′-dihydroxy-1,1′-biaryls;
 synthesis and copper-free cycloaddition with azides
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00991G
_journal_year                    2017
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-04 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.81826(15)
_cell_length_b                   9.23296(10)
_cell_length_c                   8.32936(9)
_cell_measurement_reflns_used    5956
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.9170
_cell_measurement_theta_min      5.3140
_cell_volume                     1216.50(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.71 -38.00   0.00   99
  2  ω     18.00  98.00   1.00    1.00    --   41.71-125.00  60.00   80
  3  ω    100.00 178.00   1.00    4.00    --  114.00 111.00 -60.00   78
  4  ω    100.00 178.00   1.00    4.00    --  114.00 111.00   0.00   78
  5  ω     85.00 178.00   1.00    4.00    --  114.00  61.00 120.00   93
  6  ω     32.00 109.00   1.00    4.00    --  114.00 -95.00 120.00   77
  7  ω     38.00 116.00   1.00    4.00    --  114.00-111.00-120.00   78
  8  ω     86.00 178.00   1.00    4.00    --  114.00  30.00-180.00   92
  9  ω   -115.00 -14.00   1.00    1.00    --  -41.71 -57.00 -90.00  101
 10  ω   -118.00  -9.00   1.00    1.00    --  -41.71 -77.00 150.00  109
 11  ω     -4.00  83.00   1.00    1.00    --   41.71 -99.00 150.00   87
 12  ω     38.00 147.00   1.00    4.00    --  114.00 -77.00 -60.00  109
 13  ω     81.00 178.00   1.00    4.00    --  114.00  77.00  60.00   97
 14  ω     86.00 178.00   1.00    4.00    --  114.00  30.00   0.00   92
 15  ω     85.00 178.00   1.00    4.00    --  114.00  61.00 -60.00   93
 16  ω     85.00 110.00   1.00    4.00    --  114.00  61.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0728392000
_diffrn_orient_matrix_UB_12      -0.1051419000
_diffrn_orient_matrix_UB_13      -0.0386359000
_diffrn_orient_matrix_UB_21      0.0491588000
_diffrn_orient_matrix_UB_22      -0.1241992000
_diffrn_orient_matrix_UB_23      0.0807608000
_diffrn_orient_matrix_UB_31      -0.0419259000
_diffrn_orient_matrix_UB_32      0.0368569000
_diffrn_orient_matrix_UB_33      0.1619084000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9414
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.260
_diffrn_reflns_theta_min         5.548
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0072(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0370
_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)+(0.0591P)²+0.2644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1242
_reflns_number_total             1299
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob00991g2.cif
_cod_data_source_block           mw9
_cod_database_code               7155630
_chemical_oxdiff_formula         'C20 H20 O2'
_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.
;
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C3(H3)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.833
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
O7 O 0.42583(5) 0.60894(8) 0.17529(9) 0.0280(2) Uani 1 1 d .
C6 C 0.40020(7) 0.72440(11) 0.26567(13) 0.0277(3) Uani 1 1 d .
C5 C 0.31969(7) 0.72959(13) 0.33465(14) 0.0332(3) Uani 1 1 d .
H5 H 0.2818 0.6508 0.3204 0.040 Uiso 1 1 calc R
C8 C 0.39580(7) 0.46862(11) 0.22557(13) 0.0297(3) Uani 1 1 d .
H8A H 0.3433 0.4444 0.1668 0.036 Uiso 1 1 calc R
H8B H 0.3826 0.4707 0.3417 0.036 Uiso 1 1 calc R
C1 C 0.45641(7) 0.84092(11) 0.28390(12) 0.0288(3) Uani 1 1 d .
C9 C 0.46216(7) 0.35454(11) 0.19281(13) 0.0308(3) Uani 1 1 d .
H9A H 0.4834 0.3681 0.0820 0.037 Uiso 1 1 calc R
H9B H 0.4348 0.2582 0.1978 0.037 Uiso 1 1 calc R
C2 C 0.42764(8) 0.96238(12) 0.36820(15) 0.0356(3) Uani 1 1 d .
H2 H 0.4634 1.0447 0.3765 0.043 Uiso 1 1 calc R
C4 C 0.29483(8) 0.84917(14) 0.42382(15) 0.0400(3) Uani 1 1 d .
H4 H 0.2408 0.8505 0.4737 0.048 Uiso 1 1 calc R
C3 C 0.34851(8) 0.96645(14) 0.44013(15) 0.0414(3) Uani 1 1 d .
H3 H 0.3314 1.0490 0.5000 0.050 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'
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
C6 O7 C8 116.31(8) . .
O7 C6 C5 121.56(10) . .
O7 C6 C1 118.00(10) . .
C5 C6 C1 120.41(10) . .
C6 C5 H5 119.8 . .
C4 C5 C6 120.36(11) . .
C4 C5 H5 119.8 . .
O7 C8 H8A 109.6 . .
O7 C8 H8B 109.6 . .
O7 C8 C9 110.17(8) . .
H8A C8 H8B 108.1 . .
C9 C8 H8A 109.6 . .
C9 C8 H8B 109.6 . .
C6 C1 C1 123.03(8) . 3_655
C2 C1 C6 117.54(10) . .
C2 C1 C1 119.42(8) . 3_655
C8 C9 C9 115.52(9) . 3_655
C8 C9 H9A 108.4 . .
C8 C9 H9B 108.4 . .
C9 C9 H9A 108.4 3_655 .
C9 C9 H9B 108.4 3_655 .
H9A C9 H9B 107.5 . .
C1 C2 H2 118.9 . .
C3 C2 C1 122.11(11) . .
C3 C2 H2 118.9 . .
C5 C4 H4 119.9 . .
C3 C4 C5 120.11(12) . .
C3 C4 H4 119.9 . .
C2 C3 H3 120.3 . .
C4 C3 C2 119.35(11) . .
C4 C3 H3 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O7 C6 1.3666(13) .
O7 C8 1.4420(12) .
C6 C5 1.3980(16) .
C6 C1 1.4039(15) .
C5 H5 0.9500 .
C5 C4 1.3875(16) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.5119(15) .
C1 C1 1.490(2) 3_655
C1 C2 1.3992(15) .
C9 C9 1.530(2) 3_655
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C2 H2 0.9500 .
C2 C3 1.3882(19) .
C4 H4 0.9500 .
C4 C3 1.383(2) .
C3 H3 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9A O7 0.99 2.59 3.5572(14) 166.0 5_665
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
O7 C6 C5 C4 -179.00(10) . .
O7 C6 C1 C1 -3.03(17) . 3_655
O7 C6 C1 C2 176.10(9) . .
O7 C8 C9 C9 74.56(12) . 3_655
C6 O7 C8 C9 -145.81(9) . .
C6 C5 C4 C3 2.36(17) . .
C6 C1 C2 C3 3.70(16) . .
C5 C6 C1 C1 178.79(11) . 3_655
C5 C6 C1 C2 -2.07(15) . .
C5 C4 C3 C2 -0.79(18) . .
C8 O7 C6 C5 -35.67(13) . .
C8 O7 C6 C1 146.18(9) . .
C1 C6 C5 C4 -0.89(16) . .
C1 C1 C2 C3 -177.12(11) 3_655 .
C1 C2 C3 C4 -2.31(17) . .
