#------------------------------------------------------------------------------
#$Date: 2020-11-06 14:34:03 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258882 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/12/7241224.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_7241224
loop_
_publ_author_name
'Zhu, Lixiang'
'Ren, Xiaoyu'
'Du, Juan'
'Wu, Jia-Hong'
'Tan, Jian-Ping'
'Che, Jixing'
'Pan, Jianke'
'Wang, Tianli'
_publ_section_title
;
 A transition-metal-free multicomponent reaction towards constructing
 chiral 2H-1,4-benzoxazine scaffolds
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              7506
_journal_page_last               7512
_journal_paper_doi               10.1039/D0GC02134B
_journal_volume                  22
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-05-18 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.61101(18)
_cell_length_b                   10.7261(2)
_cell_length_c                   15.5952(3)
_cell_measurement_reflns_used    3753
_cell_measurement_temperature    296.63(16)
_cell_measurement_theta_max      71.4930
_cell_measurement_theta_min      4.9450
_cell_volume                     1607.69(5)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.63(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.00    --  -36.29  57.00 -60.00   84
  2  ω   -106.00  33.00   1.00    1.00    --  -36.29   0.00 -60.00  139
  3  ω      1.00  75.00   1.00    1.00    --   36.29 -99.00-120.00   74
  4  ω     88.00 173.00   1.00    1.61    --  106.21  61.00   0.00   85
  5  ω     79.00 174.00   1.00    1.61    --  106.21  77.00  90.00   95
  6  ω     37.00 109.00   1.00    1.61    --  106.21 -94.00   0.00   72
  7  ω     89.00 175.00   1.00    1.61    --  106.21  45.00 120.00   86
  8  ω     39.00 124.00   1.00    1.61    --  106.21 -61.00 150.00   85
  9  ω     68.00 177.00   1.00    1.61    --  106.21  15.00-120.00  109
 10  ω     37.00 109.00   1.00    1.61    --  106.21 -94.00-120.00   72
 11  ω     57.00 150.00   1.00    1.61    --  106.21 178.00  30.00   93
 12  ω   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00-150.00   94
 13  ω    -31.00  22.00   1.00    1.00    --   36.29 -57.00  60.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0829550000
_diffrn_orient_matrix_UB_12      -0.1227356000
_diffrn_orient_matrix_UB_13      0.0044948000
_diffrn_orient_matrix_UB_21      -0.0018229000
_diffrn_orient_matrix_UB_22      -0.0066307000
_diffrn_orient_matrix_UB_23      -0.0986731000
_diffrn_orient_matrix_UB_31      0.1371814000
_diffrn_orient_matrix_UB_32      -0.0742450000
_diffrn_orient_matrix_UB_33      0.0014005000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.704
_diffrn_reflns_theta_min         5.004
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64614
_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            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.162
_refine_ls_abs_structure_details
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0726
_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)+(0.1206P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2935
_reflns_number_total             3096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc02134b2.cif
_cod_data_source_block           wtl-zlx-p1
_cod_depositor_comments
'Adding full bibliography for 7241224--7241225.cif.'
_cod_original_cell_volume        1607.68(6)
_cod_database_code               7241224
_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 99.94
_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 N(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C005(H005), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E),
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-06-03
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.776
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O -0.1707(2) -0.6481(2) -0.32731(13) 0.0464(5) Uani 1 1 d . . . . .
O002 O -0.0242(2) -0.5569(2) -0.45917(17) 0.0546(6) Uani 1 1 d . . . . .
N003 N -0.3160(3) -0.7274(2) -0.47375(14) 0.0410(5) Uani 1 1 d . . . . .
H003 H -0.3416 -0.7405 -0.5258 0.049 Uiso 1 1 calc R . . . .
C004 C -0.1389(3) -0.5121(3) -0.45073(18) 0.0400(6) Uani 1 1 d . . . . .
C005 C -0.5434(3) -0.7641(3) -0.35465(19) 0.0446(6) Uani 1 1 d . . . . .
H005 H -0.5077 -0.8302 -0.3863 0.053 Uiso 1 1 calc R . . . .
C006 C -0.4840(3) -0.6475(2) -0.36191(16) 0.0353(6) Uani 1 1 d . . . . .
C007 C -0.1869(3) -0.4075(2) -0.50606(18) 0.0389(6) Uani 1 1 d . . . . .
C008 C -0.2387(3) -0.5622(3) -0.38269(16) 0.0385(6) Uani 1 1 d . . . . .
H008 H -0.2709 -0.4916 -0.3480 0.046 Uiso 1 1 calc R . . . .
C009 C -0.3672(3) -0.6219(3) -0.42597(16) 0.0363(6) Uani 1 1 d . . . . .
H009 H -0.4029 -0.5615 -0.4677 0.044 Uiso 1 1 calc R . . . .
C00A C -0.2922(4) -0.3259(3) -0.4817(2) 0.0500(7) Uani 1 1 d . . . . .
H00A H -0.3373 -0.3368 -0.4294 0.060 Uiso 1 1 calc R . . . .
C00B C -0.6484(3) -0.5701(4) -0.2576(2) 0.0544(8) Uani 1 1 d . . . . .
H00B H -0.6833 -0.5045 -0.2251 0.065 Uiso 1 1 calc R . . . .
C00C C -0.2236(3) -0.8074(3) -0.43251(18) 0.0407(6) Uani 1 1 d . . . . .
C00D C -0.1226(4) -0.3904(3) -0.58538(19) 0.0498(7) Uani 1 1 d . . . . .
H00D H -0.0524 -0.4444 -0.6028 0.060 Uiso 1 1 calc R . . . .
C00E C -0.5377(3) -0.5505(3) -0.3125(2) 0.0462(7) Uani 1 1 d . . . . .
H00E H -0.4984 -0.4715 -0.3165 0.055 Uiso 1 1 calc R . . . .
C00F C -0.1995(3) -0.9278(3) -0.4615(2) 0.0511(7) Uani 1 1 d . . . . .
H00F H -0.2483 -0.9577 -0.5087 0.061 Uiso 1 1 calc R . . . .
C00G C -0.1493(3) -0.7648(3) -0.36108(19) 0.0430(6) Uani 1 1 d . . . . .
C00H C -0.2662(4) -0.2128(3) -0.6133(2) 0.0608(9) Uani 1 1 d . . . . .
H00H H -0.2929 -0.1478 -0.6491 0.073 Uiso 1 1 calc R . . . .
C00I C -0.1032(4) -1.0041(3) -0.4209(3) 0.0625(10) Uani 1 1 d . . . . .
H00I H -0.0878 -1.0844 -0.4414 0.075 Uiso 1 1 calc R . . . .
C00J C -0.3301(4) -0.2280(3) -0.5353(3) 0.0605(9) Uani 1 1 d . . . . .
H00J H -0.3991 -0.1726 -0.5182 0.073 Uiso 1 1 calc R . . . .
C00K C -0.0532(3) -0.8419(4) -0.3205(2) 0.0577(9) Uani 1 1 d . . . . .
H00K H -0.0041 -0.8130 -0.2732 0.069 Uiso 1 1 calc R . . . .
C00L C -0.7072(4) -0.6871(4) -0.2511(2) 0.0573(8) Uani 1 1 d . . . . .
H00L H -0.7810 -0.7008 -0.2136 0.069 Uiso 1 1 calc R . . . .
C00M C -0.1633(4) -0.2929(4) -0.6384(2) 0.0609(9) Uani 1 1 d . . . . .
H00M H -0.1204 -0.2821 -0.6914 0.073 Uiso 1 1 calc R . . . .
C00N C -0.6561(3) -0.7838(3) -0.3005(2) 0.0560(8) Uani 1 1 d . . . . .
H00N H -0.6971 -0.8622 -0.2975 0.067 Uiso 1 1 calc R . . . .
C00O C -0.0306(4) -0.9620(4) -0.3507(3) 0.0686(11) Uani 1 1 d . . . . .
H00O H 0.0334 -1.0136 -0.3236 0.082 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'
N N 0.0311 0.0180 '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
_geom_angle_publ_flag
C00G O001 C008 115.2(2) . . ?
C009 N003 H003 121.2 . . ?
C00C N003 H003 121.2 . . ?
C00C N003 C009 117.5(2) . . ?
O002 C004 C007 121.3(3) . . ?
O002 C004 C008 120.5(3) . . ?
C007 C004 C008 118.2(2) . . ?
C006 C005 H005 119.7 . . ?
C006 C005 C00N 120.7(3) . . ?
C00N C005 H005 119.7 . . ?
C005 C006 C009 121.4(3) . . ?
C005 C006 C00E 118.6(3) . . ?
C00E C006 C009 119.9(2) . . ?
C00A C007 C004 122.8(3) . . ?
C00A C007 C00D 118.8(3) . . ?
C00D C007 C004 118.4(3) . . ?
O001 C008 C004 111.1(2) . . ?
O001 C008 H008 108.0 . . ?
O001 C008 C009 111.3(2) . . ?
C004 C008 H008 108.0 . . ?
C004 C008 C009 110.1(2) . . ?
C009 C008 H008 108.0 . . ?
N003 C009 C006 116.6(2) . . ?
N003 C009 C008 106.2(2) . . ?
N003 C009 H009 107.2 . . ?
C006 C009 C008 112.1(2) . . ?
C006 C009 H009 107.2 . . ?
C008 C009 H009 107.2 . . ?
C007 C00A H00A 120.0 . . ?
C00J C00A C007 120.1(3) . . ?
C00J C00A H00A 120.0 . . ?
C00E C00B H00B 120.0 . . ?
C00L C00B H00B 120.0 . . ?
C00L C00B C00E 120.0(3) . . ?
N003 C00C C00G 119.5(3) . . ?
C00F C00C N003 122.0(3) . . ?
C00F C00C C00G 118.5(3) . . ?
C007 C00D H00D 119.9 . . ?
C00M C00D C007 120.2(3) . . ?
C00M C00D H00D 119.9 . . ?
C006 C00E H00E 119.5 . . ?
C00B C00E C006 120.9(3) . . ?
C00B C00E H00E 119.5 . . ?
C00C C00F H00F 119.6 . . ?
C00I C00F C00C 120.8(4) . . ?
C00I C00F H00F 119.6 . . ?
O001 C00G C00C 121.7(3) . . ?
O001 C00G C00K 117.8(3) . . ?
C00K C00G C00C 120.4(3) . . ?
C00J C00H H00H 119.9 . . ?
C00M C00H H00H 119.9 . . ?
C00M C00H C00J 120.2(3) . . ?
C00F C00I H00I 119.7 . . ?
C00O C00I C00F 120.5(4) . . ?
C00O C00I H00I 119.7 . . ?
C00A C00J H00J 119.8 . . ?
C00H C00J C00A 120.4(3) . . ?
C00H C00J H00J 119.8 . . ?
C00G C00K H00K 120.0 . . ?
C00O C00K C00G 120.1(4) . . ?
C00O C00K H00K 120.0 . . ?
C00B C00L H00L 120.2 . . ?
C00B C00L C00N 119.7(3) . . ?
C00N C00L H00L 120.2 . . ?
C00D C00M H00M 119.8 . . ?
C00H C00M C00D 120.4(3) . . ?
C00H C00M H00M 119.8 . . ?
C005 C00N H00N 119.9 . . ?
C00L C00N C005 120.1(3) . . ?
C00L C00N H00N 119.9 . . ?
C00I C00O C00K 119.7(3) . . ?
C00I C00O H00O 120.1 . . ?
C00K C00O H00O 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C008 1.422(3) . ?
O001 C00G 1.374(4) . ?
O002 C004 1.210(4) . ?
N003 H003 0.8600 . ?
N003 C009 1.442(4) . ?
N003 C00C 1.392(4) . ?
C004 C007 1.488(4) . ?
C004 C008 1.528(4) . ?
C005 H005 0.9300 . ?
C005 C006 1.379(4) . ?
C005 C00N 1.389(4) . ?
C006 C009 1.528(3) . ?
C006 C00E 1.394(4) . ?
C007 C00A 1.391(4) . ?
C007 C00D 1.395(4) . ?
C008 H008 0.9800 . ?
C008 C009 1.546(4) . ?
C009 H009 0.9800 . ?
C00A H00A 0.9300 . ?
C00A C00J 1.391(5) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.382(4) . ?
C00B C00L 1.380(5) . ?
C00C C00F 1.389(4) . ?
C00C C00G 1.400(4) . ?
C00D H00D 0.9300 . ?
C00D C00M 1.390(5) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00I 1.388(5) . ?
C00G C00K 1.392(4) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.372(6) . ?
C00H C00M 1.367(6) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.375(6) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00O 1.388(6) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.382(5) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
