#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029253.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_4029253
loop_
_publ_author_name
'Koshima, Hideko'
'Fukano, Michitaro'
'Ojima, Naoko'
'Johmoto, Kohei'
'Uekusa, Hidehiro'
'Shiro, Motoo'
_publ_section_title
;
 Absolute asymmetric photocyclization of triisopropylbenzophenone
 derivatives in crystals and their morphological changes.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3088
_journal_page_last               3093
_journal_paper_doi               10.1021/jo5000913
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H35 N O2'
_chemical_formula_sum            'C30 H35 N O2'
_chemical_formula_weight         441.61
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   26.203(3)
_cell_length_b                   8.9809(9)
_cell_length_c                   11.0665(11)
_cell_measurement_reflns_used    19948
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      3.38
_cell_volume                     2604.2(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2000-2010)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku, 2000-2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25102
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952.00
_exptl_crystal_size_max          0.588
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     300
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     15
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0829P)²+0.5845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2079
_reflns_number_total             2493
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo5000913_si_004.cif
_cod_data_source_block           RGK1944[2(m-benzyl)]
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029253.cif.
;
_cod_database_code               4029253
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2+Z
3 1/2+X,1/2-Y,+Z
4 -X,-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18518(13) 0.6630(4) 0.8127(3) 0.0860(10) Uani 1.0 4 d . . .
O2 O 0.32896(10) 0.3091(3) 0.8674(3) 0.0604(7) Uani 1.0 4 d . . .
N1 N 0.15655(11) 0.7224(4) 0.6293(3) 0.0570(8) Uani 1.0 4 d . . .
H1N H 0.1611 0.7164 0.5525 0.0684 Uiso 1.0 4 calc R . .
C1 C 0.26373(13) 0.4854(4) 0.7231(4) 0.0479(8) Uani 1.0 4 d . . .
H1 H 0.2592 0.4911 0.8064 0.0575 Uiso 1.0 4 calc R . .
C2 C 0.23172(12) 0.5657(4) 0.6472(4) 0.0467(8) Uani 1.0 4 d . . .
C3 C 0.23960(15) 0.5566(5) 0.5236(4) 0.0606(10) Uani 1.0 4 d . . .
H3 H 0.2187 0.6108 0.4719 0.0728 Uiso 1.0 4 calc R . .
C4 C 0.27767(16) 0.4692(5) 0.4755(4) 0.0681(11) Uani 1.0 4 d . . .
H4 H 0.2823 0.4648 0.3923 0.0817 Uiso 1.0 4 calc R . .
C5 C 0.30897(14) 0.3884(5) 0.5511(4) 0.0562(9) Uani 1.0 4 d . . .
H5 H 0.3345 0.3284 0.5188 0.0675 Uiso 1.0 4 calc R . .
C6 C 0.30241(12) 0.3966(4) 0.6765(3) 0.0459(8) Uani 1.0 4 d . . .
C7 C 0.18952(13) 0.6543(4) 0.7036(4) 0.0514(8) Uani 1.0 4 d . . .
C8 C 0.11343(13) 0.8058(4) 0.6751(5) 0.0623(10) Uani 1.0 4 d . . .
H8A H 0.1006 0.7564 0.7469 0.0748 Uiso 1.0 4 calc R . .
H8B H 0.0865 0.8043 0.6150 0.0748 Uiso 1.0 4 calc R . .
C9 C 0.12538(13) 0.9656(4) 0.7061(4) 0.0565(9) Uani 1.0 4 d . . .
C10 C 0.10586(18) 1.0286(5) 0.8096(5) 0.0771(13) Uani 1.0 4 d . . .
H10 H 0.0857 0.9716 0.8610 0.0926 Uiso 1.0 4 calc R . .
C11 C 0.1159(3) 1.1754(6) 0.8377(6) 0.1008(19) Uani 1.0 4 d . . .
H11 H 0.1022 1.2165 0.9077 0.1210 Uiso 1.0 4 calc R . .
C12 C 0.1452(3) 1.2596(6) 0.7652(7) 0.1015(18) Uani 1.0 4 d . . .
H12 H 0.1518 1.3585 0.7847 0.1218 Uiso 1.0 4 calc R . .
C13 C 0.1651(3) 1.1986(6) 0.6627(7) 0.1031(19) Uani 1.0 4 d . . .
H13 H 0.1858 1.2560 0.6127 0.1237 Uiso 1.0 4 calc R . .
C14 C 0.15494(19) 1.0530(5) 0.6325(6) 0.0833(14) Uani 1.0 4 d . . .
H14 H 0.1682 1.0136 0.5614 0.0999 Uiso 1.0 4 calc R . .
C15 C 0.33655(12) 0.3119(4) 0.7578(3) 0.0445(8) Uani 1.0 4 d . . .
C16 C 0.38074(12) 0.2308(4) 0.7024(4) 0.0470(7) Uani 1.0 4 d . . .
C17 C 0.37489(13) 0.0829(4) 0.6646(4) 0.0538(9) Uani 1.0 4 d . . .
C18 C 0.41503(15) 0.0188(5) 0.6029(4) 0.0636(10) Uani 1.0 4 d . . .
H18 H 0.4114 -0.0787 0.5760 0.0763 Uiso 1.0 4 calc R . .
C19 C 0.46012(15) 0.0915(5) 0.5790(4) 0.0641(11) Uani 1.0 4 d . . .
C20 C 0.46499(14) 0.2359(5) 0.6185(4) 0.0638(10) Uani 1.0 4 d . . .
H20 H 0.4952 0.2866 0.6028 0.0766 Uiso 1.0 4 calc R . .
C21 C 0.42613(13) 0.3096(4) 0.6815(4) 0.0526(8) Uani 1.0 4 d . . .
C22 C 0.32651(15) -0.0046(4) 0.6897(5) 0.0641(10) Uani 1.0 4 d . . .
H22 H 0.3030 0.0625 0.7317 0.0769 Uiso 1.0 4 calc R . .
C23 C 0.3004(2) -0.0539(7) 0.5748(6) 0.1007(17) Uani 1.0 4 d . . .
H23A H 0.2966 0.0298 0.5216 0.1208 Uiso 1.0 4 calc R . .
H23B H 0.2674 -0.0939 0.5938 0.1208 Uiso 1.0 4 calc R . .
H23C H 0.3206 -0.1291 0.5359 0.1208 Uiso 1.0 4 calc R . .
C24 C 0.3361(2) -0.1337(6) 0.7721(6) 0.0984(18) Uani 1.0 4 d . . .
H24A H 0.3044 -0.1823 0.7901 0.1181 Uiso 1.0 4 calc R . .
H24B H 0.3514 -0.0987 0.8456 0.1181 Uiso 1.0 4 calc R . .
H24C H 0.3587 -0.2029 0.7333 0.1181 Uiso 1.0 4 calc R . .
C25A C 0.5042(4) 0.038(2) 0.5016(10) 0.103(4) Uiso 0.54(3) 4 d PDU A 1
H25A H 0.5019 -0.0712 0.5049 0.1241 Uiso 0.54(3) 4 calc PR A 1
C26A C 0.4957(6) 0.074(3) 0.3719(11) 0.123(5) Uiso 0.54(3) 4 d PDU A 1
H26A H 0.4607 0.0552 0.3512 0.1476 Uiso 0.54(3) 4 calc PR A 1
H26B H 0.5176 0.0142 0.3225 0.1476 Uiso 0.54(3) 4 calc PR A 1
H26C H 0.5032 0.1777 0.3584 0.1476 Uiso 0.54(3) 4 calc PR A 1
C27A C 0.5568(5) 0.071(3) 0.5424(11) 0.099(4) Uiso 0.54(3) 4 d PDU A 1
H27A H 0.5599 0.0479 0.6267 0.1192 Uiso 0.54(3) 4 calc PR A 1
H27B H 0.5638 0.1749 0.5299 0.1192 Uiso 0.54(3) 4 calc PR A 1
H27C H 0.5806 0.0123 0.4969 0.1192 Uiso 0.54(3) 4 calc PR A 1
C25B C 0.4974(4) -0.0018(15) 0.5070(9) 0.069(4) Uiso 0.46(3) 4 d PDU A 2
H25B H 0.4876 -0.1042 0.5268 0.0827 Uiso 0.46(3) 4 calc PR A 2
C26B C 0.4892(5) 0.007(2) 0.3753(9) 0.084(5) Uiso 0.46(3) 4 d PDU A 2
H26D H 0.4539 -0.0103 0.3576 0.1003 Uiso 0.46(3) 4 calc PR A 2
H26E H 0.5097 -0.0670 0.3357 0.1003 Uiso 0.46(3) 4 calc PR A 2
H26F H 0.4988 0.1041 0.3470 0.1003 Uiso 0.46(3) 4 calc PR A 2
C27B C 0.5505(5) 0.007(3) 0.5464(13) 0.094(5) Uiso 0.46(3) 4 d PDU A 2
H27D H 0.5522 -0.0073 0.6323 0.1134 Uiso 0.46(3) 4 calc PR A 2
H27E H 0.5641 0.1031 0.5262 0.1134 Uiso 0.46(3) 4 calc PR A 2
H27F H 0.5700 -0.0689 0.5066 0.1134 Uiso 0.46(3) 4 calc PR A 2
C28 C 0.43267(15) 0.4660(5) 0.7312(4) 0.0634(11) Uani 1.0 4 d . . .
H28 H 0.3987 0.5112 0.7368 0.0761 Uiso 1.0 4 calc R . .
C29 C 0.4550(3) 0.4616(7) 0.8571(6) 0.1065(19) Uani 1.0 4 d . . .
H29A H 0.4343 0.3990 0.9076 0.1278 Uiso 1.0 4 calc R . .
H29B H 0.4557 0.5605 0.8900 0.1278 Uiso 1.0 4 calc R . .
H29C H 0.4891 0.4227 0.8537 0.1278 Uiso 1.0 4 calc R . .
C30 C 0.4654(2) 0.5656(6) 0.6501(6) 0.0921(16) Uani 1.0 4 d . . .
H30A H 0.4998 0.5287 0.6487 0.1105 Uiso 1.0 4 calc R . .
H30B H 0.4651 0.6654 0.6810 0.1105 Uiso 1.0 4 calc R . .
H30C H 0.4517 0.5650 0.5696 0.1105 Uiso 1.0 4 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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, 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_publ_flag
C7 N1 C8 121.6(4) yes
C2 C1 C6 120.9(4) yes
C1 C2 C3 118.4(4) yes
C1 C2 C7 118.0(4) yes
C3 C2 C7 123.5(4) yes
C2 C3 C4 121.6(4) yes
C3 C4 C5 119.8(4) yes
C4 C5 C6 120.0(4) yes
C1 C6 C5 119.2(4) yes
C1 C6 C15 120.7(3) yes
C5 C6 C15 120.1(3) yes
O1 C7 N1 121.3(4) yes
O1 C7 C2 121.1(4) yes
N1 C7 C2 117.5(4) yes
N1 C8 C9 114.2(3) yes
C8 C9 C10 120.2(4) yes
C8 C9 C14 121.8(4) yes
C10 C9 C14 118.0(4) yes
C9 C10 C11 120.7(5) yes
C10 C11 C12 120.8(6) yes
C11 C12 C13 119.3(6) yes
C12 C13 C14 120.6(6) yes
C9 C14 C13 120.6(6) yes
O2 C15 C6 120.9(3) yes
O2 C15 C16 121.2(3) yes
C6 C15 C16 117.9(3) yes
C15 C16 C17 119.9(3) yes
C15 C16 C21 118.5(3) yes
C17 C16 C21 121.4(3) yes
C16 C17 C18 117.4(4) yes
C16 C17 C22 121.9(4) yes
C18 C17 C22 120.7(4) yes
C17 C18 C19 123.5(4) yes
C18 C19 C20 117.8(4) yes
C18 C19 C25A 127.7(7) yes
C18 C19 C25B 113.1(6) yes
C20 C19 C25A 114.2(7) yes
C20 C19 C25B 129.0(6) yes
C19 C20 C21 122.5(4) yes
C16 C21 C20 117.4(4) yes
C16 C21 C28 120.2(4) yes
C20 C21 C28 122.4(4) yes
C17 C22 C23 112.1(4) yes
C17 C22 C24 111.9(4) yes
C23 C22 C24 111.2(4) yes
C19 C25A C26A 111.0(11) yes
C19 C25A C27A 118.1(10) yes
C26A C25A C27A 112.9(11) yes
C19 C25B C26B 113.4(10) yes
C19 C25B C27B 115.3(10) yes
C26B C25B C27B 115.5(10) yes
C21 C28 C29 110.7(4) yes
C21 C28 C30 113.1(4) yes
C29 C28 C30 109.8(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.214(5) yes
O2 C15 1.229(5) yes
N1 C7 1.340(5) yes
N1 C8 1.447(5) yes
C1 C2 1.389(5) yes
C1 C6 1.389(5) yes
C2 C3 1.386(6) yes
C2 C7 1.498(5) yes
C3 C4 1.376(6) yes
C4 C5 1.378(6) yes
C5 C6 1.400(5) yes
C6 C15 1.480(5) yes
C8 C9 1.508(6) yes
C9 C10 1.375(7) yes
C9 C14 1.372(7) yes
C10 C11 1.380(8) yes
C11 C12 1.344(9) yes
C12 C13 1.364(10) yes
C13 C14 1.376(8) yes
C15 C16 1.499(5) yes
C16 C17 1.401(5) yes
C16 C21 1.403(5) yes
C17 C18 1.380(6) yes
C17 C22 1.518(6) yes
C18 C19 1.375(6) yes
C19 C20 1.375(6) yes
C19 C25A 1.518(12) yes
C19 C25B 1.513(12) yes
C20 C21 1.400(6) yes
C21 C28 1.518(6) yes
C22 C23 1.510(8) yes
C22 C24 1.496(7) yes
C25A C26A 1.489(17) yes
C25A C27A 1.479(16) yes
C25B C26B 1.475(14) yes
C25B C27B 1.460(16) yes
C28 C29 1.512(8) yes
C28 C30 1.529(7) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O2 2_554 3.025(5) 0.860 2.227 154.4 no
