#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/88/2208845.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2208845
loop_
_publ_author_name
'Saeed, Aamer'
'Flörke, Ulrich'
_publ_section_title
;
 1-(4-Chlorophenyl)-6,7-dimethoxyisochroman
;
_journal_coeditor_code           CS2001
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1819
_journal_page_last               o1821
_journal_paper_doi               10.1107/S1600536806011792
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H17 Cl O3'
_chemical_formula_moiety         'C17 H17 Cl O3'
_chemical_formula_sum            'C17 H17 Cl O3'
_chemical_formula_weight         304.76
_chemical_name_systematic
;
1-(4-Chlorophenyl)-6,7-dimethoxyisochroman
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.8770(10)
_cell_length_b                   5.3142(3)
_cell_length_c                   16.3985(9)
_cell_measurement_reflns_used    4340
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.43
_cell_volume                     1459.89(14)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13531
_diffrn_reflns_theta_full        28.08
_diffrn_reflns_theta_max         28.08
_diffrn_reflns_theta_min         1.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  420
_diffrn_standards_number         4351
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9358
_exptl_absorpt_correction_T_min  0.8954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0424
_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)+(0.0609P)²+0.562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                3050
_reflns_number_total             3531
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cs2001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208845
_cod_database_fobs_code          2208845
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.38719(2) 0.54092(9) 0.38286(3) 0.04020(14) Uani d . 1
O O1 0.74629(6) 0.2315(2) 0.30335(6) 0.0292(2) Uani d . 1
O O2 0.81316(6) 0.8414(2) 0.61986(6) 0.0275(2) Uani d . 1
O O3 0.93535(6) 0.5440(2) 0.64814(6) 0.0257(2) Uani d . 1
C C1 0.64861(8) 0.4869(3) 0.35364(8) 0.0224(3) Uani d . 1
C C2 0.60322(9) 0.6852(3) 0.31898(10) 0.0299(3) Uani d . 1
H H2A 0.6274 0.8102 0.2888 0.036 Uiso calc R 1
C C3 0.52254(9) 0.7033(3) 0.32791(10) 0.0326(3) Uani d . 1
H H3A 0.4915 0.8395 0.3040 0.039 Uiso calc R 1
C C4 0.48841(8) 0.5214(3) 0.37180(9) 0.0268(3) Uani d . 1
C C5 0.53228(9) 0.3215(3) 0.40710(9) 0.0289(3) Uani d . 1
H H5A 0.5078 0.1968 0.4372 0.035 Uiso calc R 1
C C6 0.61262(8) 0.3064(3) 0.39775(9) 0.0270(3) Uani d . 1
H H6A 0.6435 0.1703 0.4220 0.032 Uiso calc R 1
C C7 0.73616(8) 0.4658(3) 0.34375(9) 0.0246(3) Uani d . 1
H H7A 0.7504 0.6054 0.3073 0.029 Uiso calc R 1
C C8 0.82828(9) 0.1903(3) 0.29347(9) 0.0314(3) Uani d . 1
H H8A 0.8500 0.3408 0.2683 0.038 Uiso calc R 1
H H8B 0.8327 0.0457 0.2562 0.038 Uiso calc R 1
C C9 0.87619(9) 0.1379(3) 0.37581(9) 0.0275(3) Uani d . 1
H H9A 0.8640 -0.0337 0.3942 0.033 Uiso calc R 1
H H9B 0.9339 0.1458 0.3701 0.033 Uiso calc R 1
C C10 0.85689(8) 0.3271(3) 0.43923(8) 0.0226(3) Uani d . 1
C C11 0.79063(8) 0.4813(3) 0.42494(8) 0.0213(3) Uani d . 1
C C12 0.77495(8) 0.6579(3) 0.48436(8) 0.0221(3) Uani d . 1
H H12A 0.7299 0.7655 0.4739 0.027 Uiso calc R 1
C C13 0.82405(8) 0.6780(3) 0.55810(8) 0.0216(3) Uani d . 1
C C14 0.89049(8) 0.5168(3) 0.57309(9) 0.0213(3) Uani d . 1
C C15 0.90621(8) 0.3459(3) 0.51397(9) 0.0231(3) Uani d . 1
H H15A 0.9514 0.2388 0.5241 0.028 Uiso calc R 1
C C16 0.74778(9) 1.0131(3) 0.60433(9) 0.0274(3) Uani d . 1
H H16A 0.7564 1.1226 0.5581 0.041 Uiso calc R 1
H H16B 0.7441 1.1158 0.6534 0.041 Uiso calc R 1
H H16C 0.6981 0.9184 0.5909 0.041 Uiso calc R 1
C C17 0.99185(9) 0.3487(3) 0.67008(9) 0.0286(3) Uani d . 1
H H17A 0.9653 0.1849 0.6627 0.043 Uiso calc R 1
H H17B 1.0143 0.3686 0.7277 0.043 Uiso calc R 1
H H17C 1.0348 0.3583 0.6350 0.043 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_publ_flag
C8 O1 C7 110.94(11) y
C13 O2 C16 116.39(11) ?
C14 O3 C17 115.40(11) ?
C2 C1 C6 119.07(13) ?
C2 C1 C7 120.84(13) ?
C6 C1 C7 120.10(12) ?
C1 C2 C3 120.66(14) ?
C1 C2 H2A 119.7 ?
C3 C2 H2A 119.7 ?
C4 C3 C2 119.01(14) ?
C4 C3 H3A 120.5 ?
C2 C3 H3A 120.5 ?
C3 C4 C5 121.57(14) ?
C3 C4 Cl1 119.44(12) ?
C5 C4 Cl1 118.99(12) ?
C4 C5 C6 118.71(14) ?
C4 C5 H5A 120.6 ?
C6 C5 H5A 120.6 ?
C1 C6 C5 120.99(14) ?
C1 C6 H6A 119.5 ?
C5 C6 H6A 119.5 ?
O1 C7 C1 106.73(11) y
O1 C7 C11 110.98(12) y
C1 C7 C11 113.34(11) y
O1 C7 H7A 108.6 ?
C1 C7 H7A 108.6 ?
C11 C7 H7A 108.6 ?
O1 C8 C9 110.30(11) ?
O1 C8 H8A 109.6 ?
C9 C8 H8A 109.6 ?
O1 C8 H8B 109.6 ?
C9 C8 H8B 109.6 ?
H8A C8 H8B 108.1 ?
C10 C9 C8 110.83(12) ?
C10 C9 H9A 109.5 ?
C8 C9 H9A 109.5 ?
C10 C9 H9B 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 108.1 ?
C11 C10 C15 119.28(13) ?
C11 C10 C9 121.00(13) ?
C15 C10 C9 119.72(13) ?
C10 C11 C12 119.73(13) ?
C10 C11 C7 120.34(12) ?
C12 C11 C7 119.90(12) ?
C13 C12 C11 121.04(12) ?
C13 C12 H12A 119.5 ?
C11 C12 H12A 119.5 ?
O2 C13 C12 125.29(12) ?
O2 C13 C14 115.71(12) ?
C12 C13 C14 118.99(12) ?
O3 C14 C15 124.64(12) ?
O3 C14 C13 115.67(12) ?
C15 C14 C13 119.68(13) ?
C14 C15 C10 121.25(13) ?
C14 C15 H15A 119.4 ?
C10 C15 H15A 119.4 ?
O2 C16 H16A 109.5 ?
O2 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
O2 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
O3 C17 H17A 109.5 ?
O3 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O3 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.7427(15) y
O1 C8 1.4294(17) y
O1 C7 1.4302(18) y
O2 C13 1.3633(16) ?
O2 C16 1.4306(16) ?
O3 C14 1.3720(17) ?
O3 C17 1.4259(17) ?
C1 C2 1.384(2) ?
C1 C6 1.385(2) ?
C1 C7 1.5102(19) y
C2 C3 1.390(2) ?
C2 H2A 0.9500 ?
C3 C4 1.373(2) ?
C3 H3A 0.9500 ?
C4 C5 1.381(2) ?
C5 C6 1.385(2) ?
C5 H5A 0.9500 ?
C6 H6A 0.9500 ?
C7 C11 1.5255(19) ?
C7 H7A 1.0000 ?
C8 C9 1.513(2) ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 C10 1.5100(19) ?
C9 H9A 0.9900 ?
C9 H9B 0.9900 ?
C10 C11 1.3832(19) ?
C10 C15 1.399(2) ?
C11 C12 1.4012(19) ?
C12 C13 1.3848(19) ?
C12 H12A 0.9500 ?
C13 C14 1.4091(18) ?
C14 C15 1.377(2) ?
C15 H15A 0.9500 ?
C16 H16A 0.9800 ?
C16 H16B 0.9800 ?
C16 H16C 0.9800 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
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_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C16 H16B O1 4_576 0.98 2.59 3.5375(19) 164
C16 H16B Cl1 3_676 0.98 2.88 3.3115(14) 108
C16 H16C Cl1 3_666 0.98 2.89 3.7440(17) 146
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_publ_flag
C6 C1 C2 C3 -0.2(2) ?
C7 C1 C2 C3 179.70(14) ?
C1 C2 C3 C4 0.1(2) ?
C2 C3 C4 C5 0.0(2) ?
C2 C3 C4 Cl1 -179.58(12) ?
C3 C4 C5 C6 0.2(2) ?
Cl1 C4 C5 C6 179.69(12) ?
C2 C1 C6 C5 0.3(2) ?
C7 C1 C6 C5 -179.59(14) ?
C4 C5 C6 C1 -0.3(2) ?
C8 O1 C7 C1 -178.15(12) ?
C8 O1 C7 C11 -54.21(15) ?
C2 C1 C7 O1 -120.43(14) ?
C6 C1 C7 O1 59.50(17) ?
C2 C1 C7 C11 117.11(15) y
C6 C1 C7 C11 -62.97(17) ?
C7 O1 C8 C9 70.22(16) ?
O1 C8 C9 C10 -47.17(17) ?
C8 C9 C10 C11 14.14(18) ?
C8 C9 C10 C15 -166.42(12) ?
C15 C10 C11 C12 1.6(2) ?
C9 C10 C11 C12 -178.95(12) ?
C15 C10 C11 C7 179.60(12) ?
C9 C10 C11 C7 -1.0(2) ?
O1 C7 C11 C10 19.95(17) ?
C1 C7 C11 C10 140.02(13) ?
O1 C7 C11 C12 -162.06(12) ?
C1 C7 C11 C12 -41.99(17) ?
C10 C11 C12 C13 -1.1(2) ?
C7 C11 C12 C13 -179.15(12) ?
C16 O2 C13 C12 -3.4(2) ?
C16 O2 C13 C14 177.65(12) y
C11 C12 C13 O2 -179.17(13) ?
C11 C12 C13 C14 -0.2(2) ?
C17 O3 C14 C15 -12.33(19) ?
C17 O3 C14 C13 167.44(12) y
O2 C13 C14 O3 0.39(18) ?
C12 C13 C14 O3 -178.65(12) ?
O2 C13 C14 C15 -179.83(12) ?
C12 C13 C14 C15 1.1(2) ?
O3 C14 C15 C10 179.09(13) ?
C13 C14 C15 C10 -0.7(2) ?
C11 C10 C15 C14 -0.7(2) ?
C9 C10 C15 C14 179.84(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9841377
