#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003782.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_2003782
loop_
_publ_author_name
'Blake, A. J.'
'Harding, M.'
'Sharp, J. T.'
_publ_section_title
;
 4-Substituted 1-Methyl-1H-2,3-benzodiazepine Compounds
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1621
_journal_page_last               1627
_journal_paper_doi               10.1107/S0108270195001120
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C16 H22 N2 O'
_chemical_formula_sum            'C16 H22 N2 O'
_chemical_formula_weight         258.36
_chemical_melting_point          381.0(5)
_chemical_name_systematic
;
 1(S)-methyl-4(1'(R)-methoxy-2',2'-dimethylpropyl)-1H-2,3-benzodiazepine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                102.929(8)
_cell_angle_beta                 101.797(6)
_cell_angle_gamma                100.792(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7357(9)
_cell_length_b                   9.4583(10)
_cell_length_c                   11.0128(13)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      15
_cell_volume                     745.48(15)
_computing_cell_refinement       'DIF4 (Stoe & Cie, 1990a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1990b)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1992)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Stoe Stadi-4 four-circle diffractometer'
_diffrn_measurement_method
;
ω-2θ scans with ω width (0.99 + 0.35tanθ)o
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0036
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2054
_diffrn_reflns_theta_max         22.52
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       Tabular
_exptl_crystal_F_000             280
_exptl_crystal_size_max          1.23
_exptl_crystal_size_mid          1.04
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.105
_refine_ls_extinction_coef       0.120(9)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.096
_refine_ls_goodness_of_fit_obs   1.132
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_restrained_S_obs      1.132
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_obs          0.0336
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;calc w = 1/[s^2^(Fo^2^) + (0.0466P)^2^ + 0.1211P]
where P = (Fo^2^ + 2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.0991
_refine_ls_wR_factor_obs         0.0925
_reflns_number_observed          1777
_reflns_number_total             1950
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ha1139.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '380.5-381.5K' was changed to
'381.0(5)' - the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2003782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
C1 1 0.2840(2) 0.5722(2) 0.43458(13) 0.0511(4) Uani d . C
H1 1 0.4060(2) 0.6170(2) 0.42895(13) 0.061 Uiso calc R H
C1m 1 0.2833(2) 0.6031(2) 0.57589(14) 0.0650(5) Uani d . C
H1MA 1 0.3198(2) 0.7090(2) 0.61536(14) 0.098 Uiso calc R H
H1MB 1 0.3666(2) 0.5555(2) 0.61882(14) 0.098 Uiso calc R H
H1MC 1 0.1629(2) 0.5643(2) 0.58281(14) 0.098 Uiso calc R H
N2 1 0.1523(2) 0.64690(14) 0.37097(12) 0.0559(4) Uani d . N
N3 1 0.1771(2) 0.68256(14) 0.27155(11) 0.0543(4) Uani d . N
C4 1 0.3074(2) 0.6394(2) 0.20650(12) 0.0480(4) Uani d . C
C41 1 0.3852(2) 0.7549(2) 0.14410(12) 0.0505(4) Uani d . C
H41 1 0.3016(2) 0.8203(2) 0.13571(12) 0.061 Uiso calc R H
O41 1 0.39882(14) 0.68759(12) 0.01798(9) 0.0601(3) Uani d . O
C42 1 0.2287(3) 0.6396(2) -0.0758(2) 0.0785(6) Uani d . C
H42A 1 0.2463(3) 0.5955(2) -0.1584(2) 0.118 Uiso calc R H
H42B 1 0.1777(3) 0.7239(2) -0.0803(2) 0.118 Uiso calc R H
H42C 1 0.1472(3) 0.5670(2) -0.0522(2) 0.118 Uiso calc R H
C43 1 0.5749(2) 0.8544(2) 0.22186(13) 0.0526(4) Uani d . C
C44 1 0.7176(2) 0.7631(2) 0.2267(2) 0.0671(5) Uani d . C
H44A 1 0.6849(2) 0.6853(2) 0.2668(2) 0.101 Uiso calc R H
H44B 1 0.8342(2) 0.8272(2) 0.2757(2) 0.101 Uiso calc R H
H44C 1 0.7237(2) 0.7194(2) 0.1406(2) 0.101 Uiso calc R H
C45 1 0.5666(3) 0.9269(2) 0.35905(14) 0.0691(5) Uani d . C
H45A 1 0.4765(3) 0.9843(2) 0.35543(14) 0.104 Uiso calc R H
H45B 1 0.6834(3) 0.9915(2) 0.40696(14) 0.104 Uiso calc R H
H45C 1 0.5348(3) 0.8505(2) 0.40066(14) 0.104 Uiso calc R H
C46 1 0.6249(2) 0.9788(2) 0.1583(2) 0.0648(5) Uani d . C
H46A 1 0.5342(2) 1.0356(2) 0.1558(2) 0.097 Uiso calc R H
H46B 1 0.6308(2) 0.9357(2) 0.0721(2) 0.097 Uiso calc R H
H46C 1 0.7413(2) 1.0435(2) 0.2071(2) 0.097 Uiso calc R H
C5 1 0.3254(2) 0.4978(2) 0.17842(13) 0.0519(4) Uani d . C
H5 1 0.3897(2) 0.4731(2) 0.11733(13) 0.062 Uiso calc R H
C5a 1 0.2562(2) 0.3798(2) 0.23245(14) 0.0519(4) Uani d . C
C6 1 0.2187(2) 0.2300(2) 0.1614(2) 0.0670(5) Uani d . C
H6 1 0.2383(2) 0.2074(2) 0.0795(2) 0.080 Uiso calc R H
C7 1 0.1536(2) 0.1162(2) 0.2109(2) 0.0772(5) Uani d . C
H7 1 0.1286(2) 0.0173(2) 0.1625(2) 0.093 Uiso calc R H
C8 1 0.1252(2) 0.1489(2) 0.3332(2) 0.0747(5) Uani d . C
H8 1 0.0811(2) 0.0715(2) 0.3665(2) 0.090 Uiso calc R H
C9 1 0.1614(2) 0.2943(2) 0.4054(2) 0.0630(4) Uani d . C
H9 1 0.1401(2) 0.3147(2) 0.4869(2) 0.076 Uiso calc R H
C9a 1 0.2301(2) 0.4119(2) 0.35787(13) 0.0504(4) Uani d . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.0016
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.0000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.0033
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.0060
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
N2 C1 C9a 106.38(11) y
N2 C1 C1m 107.97(11) ?
C9a C1 C1m 116.68(13) ?
N3 N2 C1 117.86(11) y
N2 N3 C4 124.07(12) y
C5 C4 N3 122.05(13) y
C5 C4 C41 123.28(12) ?
N3 C4 C41 112.89(12) ?
O41 C41 C4 111.79(12) ?
O41 C41 C43 107.56(11) ?
C4 C41 C43 114.09(11) ?
C42 O41 C41 113.19(12) ?
C44 C43 C46 110.16(13) ?
C44 C43 C45 109.83(13) ?
C46 C43 C45 108.13(13) ?
C44 C43 C41 110.98(12) ?
C46 C43 C41 108.52(12) ?
C45 C43 C41 109.16(12) ?
C4 C5 C5a 127.38(13) y
C6 C5a C9a 118.70(14) ?
C6 C5a C5 119.98(14) ?
C9a C5a C5 121.29(13) y
C7 C6 C5a 121.0(2) ?
C6 C7 C8 119.9(2) ?
C9 C8 C7 120.5(2) ?
C8 C9 C9a 120.6(2) ?
C9 C9a C5a 119.19(14) ?
C9 C9a C1 123.45(13) ?
C5a C9a C1 117.34(13) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 1.492(2) y
C1 C9a 1.494(2) y
C1 C1m 1.519(2) ?
N2 N3 1.255(2) y
N3 C4 1.419(2) y
C4 C5 1.345(2) y
C4 C41 1.512(2) ?
C41 O41 1.426(2) ?
C41 C43 1.543(2) ?
O41 C42 1.420(2) ?
C43 C44 1.523(2) ?
C43 C46 1.528(2) ?
C43 C45 1.533(2) ?
C5 C5a 1.446(2) y
C5a C6 1.400(2) ?
C5a C9a 1.411(2) y
C6 C7 1.372(2) ?
C7 C8 1.384(3) ?
C8 C9 1.370(2) ?
C9 C9a 1.395(2) ?
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
C9a C1 N2 N3 -79.4(2) y
C1m C1 N2 N3 154.67(14) ?
C1 N2 N3 C4 8.5(2) y
N2 N3 C4 C5 46.9(2) y
N2 N3 C4 C41 -147.84(13) ?
C5 C4 C41 O41 27.9(2) ?
N3 C4 C41 O41 -137.16(12) ?
C5 C4 C41 C43 -94.4(2) ?
N3 C4 C41 C43 100.52(13) ?
C4 C41 O41 C42 75.92(15) ?
C43 C41 O41 C42 -158.09(12) ?
O41 C41 C43 C44 -57.93(15) ?
C4 C41 C43 C44 66.68(15) ?
O41 C41 C43 C46 63.25(14) ?
C4 C41 C43 C46 -172.14(12) ?
O41 C41 C43 C45 -179.11(11) ?
C4 C41 C43 C45 -54.5(2) ?
N3 C4 C5 C5a -16.2(2) y
C41 C4 C5 C5a -179.91(13) ?
C4 C5 C5a C6 153.7(2) ?
C4 C5 C5a C9a -28.1(2) y
C9a C5a C6 C7 1.6(2) ?
C5 C5a C6 C7 179.76(14) ?
C5a C6 C7 C8 -0.4(3) ?
C6 C7 C8 C9 0.0(3) ?
C7 C8 C9 C9a -0.9(2) ?
C8 C9 C9a C5a 2.1(2) ?
C8 C9 C9a C1 -175.90(14) ?
C6 C5a C9a C9 -2.4(2) ?
C5 C5a C9a C9 179.44(12) ?
C6 C5a C9a C1 175.71(13) ?
C5 C5a C9a C1 -2.4(2) y
N2 C1 C9a C9 -113.13(14) ?
C1m C1 C9a C9 7.4(2) ?
N2 C1 C9a C5a 68.84(15) y
C1m C1 C9a C5a -170.66(13) ?
