#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:45:42 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222641 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034081.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_4034081
loop_
_publ_author_name
'Ramesh, Perla'
'Satyanarayana, Gedu'
_publ_section_title
;
 Palladium-Catalyzed Aerobic Oxidative Coupling of
 ortho-(Alkynyl)styrenes with Allylic Alcohols via
 6-endo-dig Cyclization: Regioselective Construction of
 Polysubstituted Naphthalenes.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12856
_journal_page_last               12870
_journal_paper_doi               10.1021/acs.joc.9b01240
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C33 H28 O3'
_chemical_formula_sum            'C33 H28 O3'
_chemical_formula_weight         472.59
_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_creation_date             2018-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.8742(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.19794(19)
_cell_length_b                   17.6415(3)
_cell_length_c                   14.5974(3)
_cell_measurement_reflns_used    3616
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.8020
_cell_measurement_theta_min      4.0110
_cell_volume                     2538.18(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9805
_diffrn_measured_fraction_theta_max 0.9805
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     11.00  64.00   1.00    1.00    --    0.00  57.00  90.00   53
  2  ω    -20.00   7.00   1.00    1.00    --    0.00  57.00  90.00   27
  3  ω     13.00  40.00   1.00    1.00    --    0.00  38.00-120.00   27
  4  ω     -9.00  62.00   1.00    1.51    --   54.00 -57.00-180.00   71
  5  ω     40.00  96.00   1.00    1.51    --   54.00  57.00 150.00   56
  6  ω     47.00  91.00   1.00    1.51    --   54.00-125.00   0.00   44
  7  ω      0.00  81.00   1.00    1.51    --   54.00 -38.00   0.00   81
  8  ω     57.00 106.00   1.00    1.51    --   54.00  57.00   0.00   49
  9  ω     58.00 100.00   1.00    1.51    --  108.00 178.00   0.00   42
 10  ω    132.00 170.00   1.00    1.51    --  108.00  77.00 -30.00   38
 11  ω     37.00  81.00   1.00    1.51    --  108.00 -77.00-120.00   44
 12  ω     37.00 108.00   1.00    1.51    --  108.00-111.00 -30.00   71
 13  ω     38.00 132.00   1.00    1.51    --  108.00 -38.00 -30.00   94
 14  ω     75.00 100.00   1.00    1.51    --  108.00  25.00 150.00   25
 15  ω    142.00 178.00   1.00    1.51    --  108.00  25.00 150.00   36
 16  ω     98.00 135.00   1.00    1.51    --  108.00 -77.00-120.00   37
 17  ω     38.00 109.00   1.00    1.51    --  108.00-111.00-150.00   71
 18  ω    115.00 167.00   1.00    1.51    --  108.00  63.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0710187000
_diffrn_orient_matrix_UB_12      -0.0218602000
_diffrn_orient_matrix_UB_13      -0.1030106000
_diffrn_orient_matrix_UB_21      -0.0281784000
_diffrn_orient_matrix_UB_22      0.0843405000
_diffrn_orient_matrix_UB_23      -0.0248329000
_diffrn_orient_matrix_UB_31      0.1363159000
_diffrn_orient_matrix_UB_32      0.0059278000
_diffrn_orient_matrix_UB_33      -0.0265602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9569
_diffrn_reflns_theta_full        69.9863
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.01
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2366
_exptl_crystal_description       block
_exptl_crystal_F_000             1003.0469
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.1667
_refine_diff_density_min         -0.2343
_refine_diff_density_rms         0.0538
_refine_ls_d_res_high            0.8205
_refine_ls_d_res_low             11.0182
_refine_ls_goodness_of_fit_ref   1.0894
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0894
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0620P)²+0.1150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -12
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -8
_reflns_number_gt                3544
_reflns_number_total             4725
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b01240_si_002.cif
_cod_data_source_block           exp_8735
_cod_original_cell_volume        2538.17(8)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4034081
_chemical_oxdiff_formula         'C33 H28 O3'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C23(H23a,H23b), C24(H24a,H24b)
2.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C27(H27), C31(H31), C3(H3), C15(H15), C14(H14), C13(H13), C12(H12),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C6(H6), C7(H7), C8(H8),
 C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c), C33(H33a,H33b,H33c)
;
_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.802
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
O2 O 0.15240(12) 0.33462(7) 0.92392(8) 0.0548(3) Uani 1.000000 .
O1 O 0.36236(13) 0.52441(8) 0.73868(8) 0.0580(3) Uani 1.000000 .
C5 C 0.26631(15) 0.56904(9) 0.12763(10) 0.0409(4) Uani 1.000000 .
C16 C 0.31303(16) 0.58992(9) 0.39660(10) 0.0410(3) Uani 1.000000 .
C31 C 0.23026(15) 0.40540(10) 0.80485(11) 0.0431(4) Uani 1.000000 .
O3 O 0.01324(16) 0.24391(9) 0.80156(10) 0.0766(5) Uani 1.000000 .
C26 C 0.23382(17) 0.41232(10) 0.70963(11) 0.0472(4) Uani 1.000000 .
C4 C 0.26488(15) 0.55355(9) 0.22813(10) 0.0414(4) Uani 1.000000 .
C25 C 0.31408(16) 0.47445(10) 0.68244(11) 0.0458(4) Uani 1.000000 .
C30 C 0.15804(16) 0.34846(10) 0.83306(11) 0.0443(4) Uani 1.000000 .
C2 C 0.18217(15) 0.47694(9) 0.34086(11) 0.0422(4) Uani 1.000000 .
C1 C 0.23740(15) 0.52587(9) 0.41451(10) 0.0411(4) Uani 1.000000 .
C17 C 0.10765(16) 0.40682(10) 0.35420(11) 0.0446(4) Uani 1.000000 .
C3 C 0.19448(16) 0.49277(10) 0.24841(11) 0.0452(4) Uani 1.000000 .
C23 C 0.21414(16) 0.51412(10) 0.51189(10) 0.0447(4) Uani 1.000000 .
C15 C 0.37398(17) 0.64280(10) 0.46880(11) 0.0492(4) Uani 1.000000 .
C14 C 0.44851(19) 0.70249(11) 0.45135(13) 0.0555(4) Uani 1.000000 .
C10 C 0.38075(16) 0.56147(11) 0.09469(11) 0.0487(4) Uani 1.000000 .
C11 C 0.33008(16) 0.60305(9) 0.30377(10) 0.0417(4) Uani 1.000000 .
C24 C 0.33502(16) 0.47676(11) 0.58294(11) 0.0489(4) Uani 1.000000 .
C29 C 0.08174(19) 0.29744(11) 0.76602(13) 0.0562(5) Uani 1.000000 .
C9 C 0.37601(18) 0.57523(11) 0.00079(12) 0.0551(5) Uani 1.000000 .
C22 C 0.17605(19) 0.34417(11) 0.40051(12) 0.0546(4) Uani 1.000000 .
C12 C 0.40804(19) 0.66560(10) 0.28894(12) 0.0535(4) Uani 1.000000 .
C6 C 0.14668(18) 0.59016(12) 0.06355(12) 0.0590(5) Uani 1.000000 .
C8 C 0.2570(2) 0.59624(11) -0.06192(12) 0.0570(5) Uani 1.000000 .
C28 C 0.0837(2) 0.30462(13) 0.67224(14) 0.0722(6) Uani 1.000000 .
C27 C 0.1606(2) 0.36095(12) 0.64502(13) 0.0669(5) Uani 1.000000 .
C13 C 0.4672(2) 0.71367(11) 0.36062(13) 0.0598(5) Uani 1.000000 .
C21 C 0.1061(2) 0.27969(11) 0.41424(14) 0.0647(5) Uani 1.000000 .
C18 C -0.03248(18) 0.40241(11) 0.31868(13) 0.0556(4) Uani 1.000000 .
C19 C -0.1016(2) 0.33789(12) 0.33264(16) 0.0686(6) Uani 1.000000 .
C20 C -0.0327(2) 0.27696(12) 0.38082(15) 0.0703(6) Uani 1.000000 .
C32 C 0.2287(2) 0.38211(13) 0.99606(12) 0.0659(6) Uani 1.000000 .
C7 C 0.1423(2) 0.60365(13) -0.03049(13) 0.0655(5) Uani 1.000000 .
C33 C -0.0716(3) 0.19313(16) 0.73599(18) 0.0962(9) Uani 1.000000 .
H28 H 0.0332(2) 0.27153(13) 0.62715(14) 0.0867(7) Uiso 1.000000 R
H27 H 0.1629(2) 0.36423(12) 0.58186(13) 0.0803(7) Uiso 1.000000 R
H31 H 0.27757(15) 0.43994(10) 0.84932(11) 0.0517(4) Uiso 1.000000 R
H3 H 0.15277(16) 0.46035(10) 0.19933(11) 0.0543(5) Uiso 1.000000 R
H15 H 0.36249(17) 0.63633(10) 0.52949(11) 0.0590(5) Uiso 1.000000 R
H14 H 0.48723(19) 0.73602(11) 0.49993(13) 0.0667(5) Uiso 1.000000 R
H13 H 0.5199(2) 0.75386(11) 0.34932(13) 0.0717(6) Uiso 1.000000 R
H12 H 0.41940(19) 0.67428(10) 0.22860(12) 0.0642(5) Uiso 1.000000 R
H18 H -0.07984(18) 0.44312(11) 0.28537(13) 0.0667(5) Uiso 1.000000 R
H19 H -0.1953(2) 0.33565(12) 0.30928(16) 0.0823(7) Uiso 1.000000 R
H20 H -0.0799(2) 0.23395(12) 0.39079(15) 0.0844(7) Uiso 1.000000 R
H21 H 0.1529(2) 0.23824(11) 0.44606(14) 0.0776(6) Uiso 1.000000 R
H22 H 0.27006(19) 0.34548(11) 0.42261(12) 0.0655(5) Uiso 1.000000 R
H6 H 0.06803(18) 0.59536(12) 0.08408(12) 0.0708(6) Uiso 1.000000 R
H7 H 0.0610(2) 0.61781(13) -0.07255(13) 0.0785(7) Uiso 1.000000 R
H8 H 0.2543(2) 0.60537(11) -0.12513(12) 0.0684(6) Uiso 1.000000 R
H9 H 0.45437(18) 0.57018(11) -0.02012(12) 0.0661(5) Uiso 1.000000 R
H10 H 0.46219(16) 0.54691(11) 0.13623(11) 0.0584(5) Uiso 1.000000 R
H23a H 0.19590(16) 0.56282(10) 0.53689(10) 0.0536(5) Uiso 1.000000 R
H23b H 0.13441(16) 0.48262(10) 0.50588(10) 0.0536(5) Uiso 1.000000 R
H24a H 0.41712(16) 0.50490(11) 0.58402(11) 0.0587(5) Uiso 1.000000 R
H24b H 0.34667(16) 0.42551(11) 0.56228(11) 0.0587(5) Uiso 1.000000 R
H32a H 0.1974(11) 0.43342(19) 0.9845(6) 0.0988(8) Uiso 1.000000 GR
H32b H 0.2176(13) 0.3658(6) 1.05635(17) 0.0988(8) Uiso 1.000000 GR
H32c H 0.3228(3) 0.3795(7) 0.9964(7) 0.0988(8) Uiso 1.000000 GR
H33a H -0.1390(14) 0.22158(18) 0.6911(9) 0.1444(13) Uiso 1.000000 GR
H33b H -0.0174(4) 0.1649(9) 0.7030(11) 0.1444(13) Uiso 1.000000 GR
H33c H -0.1154(17) 0.1588(8) 0.7697(2) 0.1444(13) 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
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'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'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'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
C32 O2 C30 117.78(13)
C10 C5 C4 123.15(13)
C6 C5 C4 118.89(14)
C6 C5 C10 117.95(15)
C15 C16 C1 122.37(14)
C11 C16 C1 120.29(14)
C11 C16 C15 117.34(15)
C30 C31 C26 120.91(15)
C33 O3 C29 117.61(16)
C25 C26 C31 119.05(15)
C27 C26 C31 118.14(16)
C27 C26 C25 122.80(15)
C3 C4 C5 119.63(14)
C11 C4 C5 121.72(14)
C11 C4 C3 118.57(14)
C26 C25 O1 120.65(15)
C24 C25 O1 119.48(16)
C24 C25 C26 119.86(15)
C31 C30 O2 125.70(15)
C29 C30 O2 114.06(15)
C29 C30 C31 120.23(14)
C17 C2 C1 122.46(14)
C3 C2 C1 120.05(15)
C3 C2 C17 117.49(14)
C2 C1 C16 118.89(14)
C23 C1 C16 120.12(14)
C23 C1 C2 120.95(14)
C22 C17 C2 121.04(15)
C18 C17 C2 120.46(16)
C18 C17 C22 118.49(17)
C2 C3 C4 122.86(15)
C24 C23 C1 113.55(13)
C14 C15 C16 121.78(15)
C13 C14 C15 120.31(17)
C9 C10 C5 120.83(15)
C4 C11 C16 119.18(14)
C12 C11 C16 118.92(14)
C12 C11 C4 121.88(14)
C23 C24 C25 111.71(13)
C30 C29 O3 115.26(15)
C28 C29 O3 125.74(17)
C28 C29 C30 119.00(17)
C8 C9 C10 120.67(16)
C21 C22 C17 120.79(18)
C13 C12 C11 121.72(16)
C7 C6 C5 121.03(17)
C7 C8 C9 119.26(16)
C27 C28 C29 120.24(18)
C28 C27 C26 121.43(17)
C12 C13 C14 119.90(17)
C20 C21 C22 120.0(2)
C19 C18 C17 120.34(19)
C20 C19 C18 120.5(2)
C19 C20 C21 119.90(19)
C8 C7 C6 120.26(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C30 1.3642(19)
O2 C32 1.413(2)
O1 C25 1.219(2)
C5 C4 1.496(2)
C5 C10 1.378(2)
C5 C6 1.384(2)
C16 C1 1.429(2)
C16 C15 1.425(2)
C16 C11 1.429(2)
C31 C26 1.405(2)
C31 C30 1.370(2)
O3 C29 1.355(2)
O3 C33 1.429(2)
C26 C25 1.482(2)
C26 C27 1.381(2)
C4 C3 1.364(2)
C4 C11 1.431(2)
C25 C24 1.522(2)
C30 C29 1.408(2)
C2 C1 1.381(2)
C2 C17 1.490(2)
C2 C3 1.415(2)
C1 C23 1.514(2)
C17 C22 1.387(2)
C17 C18 1.392(2)
C23 C24 1.541(2)
C15 C14 1.361(2)
C14 C13 1.399(3)
C10 C9 1.381(2)
C11 C12 1.409(2)
C29 C28 1.380(3)
C9 C8 1.370(3)
C22 C21 1.385(3)
C12 C13 1.362(2)
C6 C7 1.383(3)
C8 C7 1.368(3)
C28 C27 1.386(3)
C21 C20 1.374(3)
C18 C19 1.381(3)
C19 C20 1.375(3)
